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[ CAS No. 207399-07-3 ] {[proInfo.proName]}

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Chemical Structure| 207399-07-3

Chemical Structure| 207399-07-3

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Quality Control of [ 207399-07-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 207399-07-3 ]

Product Details of [ 207399-07-3 ]

CAS No. :	207399-07-3	MDL No. :	MFCD00191907
Formula :	C₃₆H₄₄ClIN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	667.11	Pubchem ID :	-
Synonyms :		Chemical Name :	2-(2-(2-Chloro-3-(2-(3,3-dimethyl-1-propylindolin-2-ylidene)ethylidene)cyclohex-1-en-1-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-ium iodide

Safety of [ 207399-07-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 207399-07-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 207399-07-3 ]

[ 207399-07-3 ] Synthesis Path-Downstream 1~88

1
[ 207399-07-3 ]
[ 123-78-4 ]
C₅₄H₈₀N₃O₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2008,p. 4419 - 4421

2
[ 27578-60-5 ]
[ 207399-07-3 ]
[ 1255954-14-3 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

3
[ 51-61-6 ]
[ 207399-07-3 ]
C₄₄H₅₄N₃O₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

4
[ 107-10-8 ]
[ 207399-07-3 ]
C₃₉H₅₂N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

5
[ 89-93-0 ]
[ 207399-07-3 ]
C₄₄H₅₄N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

6
[ 2706-56-1 ]
[ 207399-07-3 ]
[ 1255954-13-2 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

7
[ 7663-77-6 ]
[ 207399-07-3 ]
C₄₃H₅₇N₄O⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

8
[ 207399-07-3 ]
[ 50541-93-0 ]
C₄₈H₆₁N₄⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

9
[ 207399-07-3 ]
[ 2016-42-4 ]
C₅₀H₇₄N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

10
[ 207399-07-3 ]
[ 15673-00-4 ]
C₄₂H₅₈N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

11
[ 207399-07-3 ]
[ 6291-85-6 ]
C₄₁H₅₆N₃O⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

12
[ 207399-07-3 ]
[ 2869-34-3 ]
C₄₉H₇₂N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

13
[ 207399-07-3 ]
[ 5397-31-9 ]
C₄₇H₆₈N₃O⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

14
[ 207399-07-3 ]
[ 5586-73-2 ]
C₅₁H₆₀N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

15
[ 207399-07-3 ]
[ 13214-66-9 ]
C₄₆H₅₈N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

16
[ 207399-07-3 ]
[ 64353-29-3 ]
C₄₆H₅₈N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

17
[ 207399-07-3 ]
[ 69385-30-4 ]
C₄₃H₅₀F₂N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

18
[ 207399-07-3 ]
[ 4393-09-3 ]
C₄₅H₅₆N₃O₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

19
[ 207399-07-3 ]
[ 39590-27-7 ]
C₄₅H₅₆N₃O⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

20
[ 207399-07-3 ]
[ 1484-85-1 ]
C₄₄H₅₂N₃O₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

21
[ 207399-07-3 ]
[ 75-04-7 ]
[ 1255954-15-4 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408
[2]Dyes and Pigments,2016,vol. 133,p. 127 - 131

22
[ 207399-07-3 ]
[ 625-30-9 ]
C₄₁H₅₆N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

23
[ 207399-07-3 ]
[ 1003-03-8 ]
C₄₁H₅₄N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

24
[ 207399-07-3 ]
[ 2039-67-0 ]
C₄₅H₅₆N₃O⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

25
[ 207399-07-3 ]
[ 5332-73-0 ]
[ 1255954-99-4 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

26
[ 61010-04-6 ]
[ 20205-29-2 ]
[ 207399-07-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	In butan-1-ol; benzene; at 160℃; for 10h;Inert atmosphere;	la (500 mg, 2.9 mmol, lequiv) and lb (1.91g, 5.81 mmol, 2 equiv) were dissolved in n-butanol (BuOH)-benzene (7:3) under N2 atmosphere, and refluxed at 160 C for 10 hours with a Dean-Stark condenser. Afterwards, the solvent was evaporated, and the resulting green solid was washed with Et20 and purified by flash chromatography (DCM-MeOH, 50:1) to obtain 1 as a green solid (1.8 g, 96%). 1H- NMR (300 MHz, CDC13) 5=1.06 (t, 6H, J=7.5 Hz), 1.31 (m, 4H), 1.64 (s, 12H), 1.95 (m, 2H), 2.73 (m, 4H), 4.15 (t, 4H, J=6.9Hz), 6.23 (d, 2H, J=14.2 Hz), 7.15-7.72 (m, 8H), 8.19 (d, 2H, J=13.8 Hz). tR: 5.64 min, ESI m/z (C36H44C1N2+), calc: 539.4; found: 539.1.
85.3%	With sodium acetate; In toluene;Inert atmosphere; Reflux; Dean-Stark;	Compound 3 (0.5 g, 2.9 mmol) and compound 4 (1.91 g, 5.81 mmol) were dissolved in BuOH-toluene (25 mL, 7:3, v:v) under Ar, and the solution was refluxed overnight in a 100-mL flask with three necks installed with a Dean-Stark condenser to remove generated water. Then, all solvents were removed under vacuum and the residual solid was purified with a flash chromatography (DCM:MeOH, 50:1 to 20:1, v:v) to give compound 4 (IR780, 1.6 g, 85.3%) as a dark green solid.
71.17%	In cyclohexane; butan-1-ol; at 100℃; for 10h;Inert atmosphere;	Starting material A (0.86 g, 5 mmol), starting material B (3.29 g, 10 mmol),Add 28 mL of n-butanol and 12 mL of cyclohexaneIn a 100 mL round bottom flask, replace N2 three times with vacuum.The temperature was raised to 100 C and refluxed for 10 hours.After cooling the reaction solution to room temperature,A large amount of metallic luster green solid is produced in the system, suction filtration, petroleum ether,The filter cake was rinsed with ethyl acetate to give 2.37 g of a gold-green solid powder.The yield was 71.17%.

In toluene; butan-1-ol; at 120℃; for 12h;Darkness;

Under ice bath conditions, POCl3 (10.5 mL, 115 mmol)Methylene chloride solution (5 mL) was slowly added to DMF (20 mL, 258 mmol)The mixture was mixed with dichloromethane (15 mL) and stirred for 0.5 h.Cyclohexanone (5 g, 50 mmol) was added dropwise to the solution.The mixed solution was refluxed for 6 hours and poured into an ice water mixture.After 12 hours, the resulting yellow crystals were filtered to give a yellow solid powder, Compound a.Dissolve in 50ml acetonitrile at room temperature2,3,3-trimethylhydrazine(2g, 12.5mmol) and propyl iodide(10.6g, 62mmol),Stir at 85 C for 15 h in the dark.The solvent was recrystallized from anhydrous diethyl ether to give a purple powder, Compound b.Compound a (0.52 g, 3 mmol, 1 equiv.), b (1.97 g, 6 mmol, 2 equiv.)The mixed solution of butanol and toluene (20 mL, 3:7, v/v) was stirred at 120 C for 12 h in the dark.After cooling to room temperature, the solvent was evaporated under reduced pressure to give a crude product, which was crystallised twice from diethyl ether.A green powder, Cy7-Cl, was obtained.

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408
[2]Patent: WO2011/119114,2011,A1 .Location in patent: Page/Page column 45
[3]Chemical Communications,2014,vol. 50,p. 6589 - 6591
[4]Journal of Controlled Release,2020,vol. 321,p. 483 - 496
[5]Patent: CN109054428,2018,A .Location in patent: Paragraph 0076; 0084; 0085; 0086
[6]Chemical Communications,2018,vol. 54,p. 1133 - 1136
[7]Patent: CN108440369,2018,A .Location in patent: Paragraph 0033; 0035; 0037; 0042; 0047; 0052

27
[ 207399-07-3 ]
[ 1262963-03-0 ]
[ 1262963-05-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 5568 - 5575

28
[ 207399-07-3 ]
[ 1262963-04-1 ]
[ 1262963-06-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 5568 - 5575

29
[ 207399-07-3 ]
[ 1262963-00-7 ]
[ 1262963-01-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 5568 - 5575

30
[ 207399-07-3 ]
[ 64318-28-1 ]
[ 1262963-07-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 5568 - 5575

31
[ 2706-56-1 ]
[ 207399-07-3 ]
[ 75-36-5 ]
[ 1255954-17-6 ]

Yield	Reaction Conditions	Operation in experiment
45%		1 (20 mg, 30 μιηο, 1 equiv) and a primary amine building block selected from FIG. 4 (120 μιηο, 4 equiv) were dissolved in ACN, and DIEA (7.7 μΙ_, 60 μϖιο, 2 equiv) was added. The reaction mixture was heated at 80 C for 10-60 minutes, depending on the reactivity of the amine. The resulting blue mixtures were neutralized with 0.1 N HC1, and concentrated under vacuum. The blue mixtures were then dissolved in DCM under N2 atmosphere, and treated with excess DIEA (96.2 μ, 750 μϖιο, 25 equiv) and acetyl chloride (11.7 μ., 150 μϖιο, 5 equiv) at 0 C for 15 minutes. The final green products were washed with 0.1 N HC1 to remove excess DIEA, concentrated under vacuum, and purified by a normal-phase silica short column using DCM-MeOH (ranging from 100:0 to 97:3) as the eluting solvent. The characterization of the whole library was performed by LCMS (Table 1 ), and selected compounds were also characterized by NMR and high-resolution mass spectrometry (HRMS).

Reference： [1]Patent: WO2011/119114,2011,A1 .Location in patent: Page/Page column 46

32
[ 1640-39-7 ]
[ 207399-07-3 ]

Reference： [1]Patent: WO2011/119114,2011,A1
[2]Chemical Communications,2014,vol. 50,p. 6589 - 6591
[3]Patent: KR2015/49824,2015,A
[4]Patent: CN108440369,2018,A
[5]Patent: CN109054428,2018,A
[6]Journal of Controlled Release,2020,vol. 321,p. 483 - 496

33
[ 25560-00-3 ]
[ 207399-07-3 ]
[ 1501-26-4 ]
[ 1313374-54-7 ]

Yield	Reaction Conditions	Operation in experiment
		1 (300 mg, 0.45 mmol, 1 equiv) and l-(3-aminopropyl)-2-pipecoline (170 mg, 0.9 mmol, 2 equiv) were dissolved in ACN (2 mL), and DIEA (87 iL, 0.67 mmol, 1.5 equiv) was added. The reaction mixture was heated at 80 C for 40 minutes, and the resulting blue mixture was neutralized with 0.1 N HCl and concentrated under vacuum. The blue mixture was dissolved in DCM under N2 atmosphere, and treated with excess DIEA (700 iL, 5.39 mmol, 12 equiv) and methyl 4- (chloroformyl)butyrate (110 μ, 0.67 mmol, 1.5 equiv) at 0 C for 15 minutes. The resulting green product 2 was washed with 0.1 N HCl and brine, concentrated under vacuum, and used without further purification.

Reference： [1]Patent: WO2011/119114,2011,A1 .Location in patent: Page/Page column 53

34
[ 108-94-1 ]
[ 207399-07-3 ]

Reference： [1]Patent: WO2011/119114,2011,A1
[2]Chemical Communications,2014,vol. 50,p. 6589 - 6591
[3]Patent: KR2015/49824,2015,A
[4]Patent: CN108440369,2018,A
[5]Patent: CN109054428,2018,A
[6]Journal of Controlled Release,2020,vol. 321,p. 483 - 496

35
[ 207399-07-3 ]
[ 54840-15-2 ]
[ 1242439-55-9 ]

Yield	Reaction Conditions	Operation in experiment
73%		Compound 4 (126 mg, 0.60 mmol) was dissolved in DMF (15 mL), the solution was added with sodium hydride (60% in oil, 24 mg, 0.60 mmol), and the mixture was stirred at room temperature for 10 minutes under an argon atmosphere. The reaction solution was added with IR-780 iodide (200 mg, 0.30 mmol) dissolved in DMF (15 mL), and the mixture was further stirred at room temperature for 16 hours. After the solvent was evaporated, the residue was purified by silica gel column chromatography (NH silica, dichloromethane/methanol, 19:1) to obtain Compound 5 (184 mg, 73%) as green solid.1H-NMR (300 MHz, CDCl3): delta 1.05 (t, J=7.4 Hz, 6H), 1.36 (s, 12H), 1.50 (s, 9H), 1.87 (sex, J=7.4 Hz, 4H), 2.05 (t, J=5.5 Hz, 2H), 2.72 (t, J=5.5 Hz, 4H), 4.05 (t, J=7.4 Hz, 4H), 6.05 (d, J=14.3 Hz, 2H), 6.80 (br s, 1H), 6.99 (d, J=9.0 Hz, 2H), 7.09 (d, J=7.7 Hz, 2H), 7.20 (d, J=7.7 Hz, 2H), 7.27 (d, J=6.8 Hz, 2H), 7.34 (d, J=6.8 Hz, 2H), 7.47 (d, J'29.0 Hz, 2H), 7.91 (d, J=14.3 Hz, 2H)LRMS (ESI+): m/z 712 (M-I)+

Reference： [1]Patent: US2012/65384,2012,A1 .Location in patent: Page/Page column 13

36
[ 207399-07-3 ]
C₃₆H₄₅ClN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In methanol; at 20℃; for 0.333333h;Inert atmosphere;	Synthesis of H-IR 780: To an oven-dried 250-mL round-bottomed flask with a stir-bar and septum under N2 were added <strong>[207399-07-3]IR-780</strong> (100 mg, 0.125 mmol), followed by methanol (100 mL). To the resulting green solution, sodium borohydride (19.0 mg, 5.0 mmol) was slowly added over 5 min. The solution turned light yellow, and the mixture was stirred (at) ambient temperature for an additional 15 min. The solvent was removed under reduced pressure, and the product was purified by CombiFlash system (i.e., automated flash chromatography) using hexane/ethyl acetate as eluent.

Reference： [1]Patent: WO2013/44156,2013,A1 .Location in patent: Paragraph 0482

37
[ 207399-07-3 ]
C₃₆H₄₄⁽²⁾HClN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium borodeuteride; In methanol; at 20℃; for 0.333333h;Inert atmosphere;	Synthesis of H-IR 780: To an oven-dried 250-mL round-bottomed flask with a stir-bar and septum under N2 were added <strong>[207399-07-3]IR-780</strong> (100 mg, 0.125 mmol), followed by methanol (100 mL). To the resulting green solution, sodium borohydride (19.0 mg, 5.0 mmol) was slowly added over 5 min. The solution turned light yellow, and the mixture was stirred (at) ambient temperature for an additional 15 min. The solvent was removed under reduced pressure, and the product was purified by CombiFlash system (i.e., automated flash chromatography) using hexane/ethyl acetate as eluent.

Reference： [1]Patent: WO2013/44156,2013,A1 .Location in patent: Paragraph 0483

38
[ 207399-07-3 ]
[ 121219-16-7 ]
[ 1428582-92-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; at 115℃; for 2h;Inert atmosphere;	To an oven dried pressure tube with a magnetic stir-bar were added <strong>[207399-07-3]IR-780</strong> (400 mg, 0.74 mmol), 2,3-difluoro phenyl boronic acid (1.17 g, 6.23 mmol), palladium (0) tetrakis (222 mg), 4.5 mL THF and 1.5 mL nano-pure water followed by 1.44 mL DIPEA. The reaction mixture was flashed with N2 and was heated to 115 C for 2 h. Mass spectral analysis indicated only the desired product with a very little peak corresponding to the decholinated starting material (m/z = 506). The product was purified using Teledyne's Isco CombiFlash system using dichloromethane/methanol as eluent.

Reference： [1]Patent: WO2013/44156,2013,A1 .Location in patent: Paragraph 0496

39
[ 110-85-0 ]
[ 207399-07-3 ]
[ 1477612-49-9 ]

Yield	Reaction Conditions	Operation in experiment
87.4%	In N,N-dimethyl-formamide; at 80℃; for 4h;	A convenient synthetic route for compound 1 from commercially available compounds was provided and depicted in Fig. 1. Compound 1: <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (52.2 mg, 0.08 mmol) and piperazine (36.4 mg, 0.4 mmol) were dissolved in dry DMF (10 mL). The reaction mixture was stirred and refluxed for 4 h at 80 C. After the solvent was evaporated under reduced pressure, the crude product was purified by silica gel column chromatography using CH2Cl2/C2H5OH (20:1, v/v) as eluent to afford a golden solid product. Yield: 41.2 mg (87.4%). 1H NMR (400 MHz, CDCl3): δ 7.67 (d, J = 12.80 Hz, 2H), 7.33 (d, J = 12.4, 2H), 7.27 (d, J = 8.2 Hz, 2H) 7.14 (d, J = 5.4 Hz, 2H), 6.96 (d, J = 6.0 Hz, 2H), 5.78 (d, J = 12.6 Hz, 2H) 4.02 (s, 4H) 3.89 (s, 4H) 3.31 (s, 4H) 2.93 (m, 2H) 2.47 (s, 4H) 1.72 (s, 12H) 1.32 (t,J = 7.3, 4H) 1.06 (t, J = 6.7 6H) 13C NMR (100 MHz, CDCl3): δ.169.1, 142.9, 141.0, 140.3, 128.3, 123.6, 123.5, 122.2, 109.2, 95.6, 55.8, 47.4, 45.2, 29.7, 28.7, 25.8, 22.6, 21.8, 11.7. MS (TOF) m/z 589.5. Anal. calcd. for C40H53N4 (1): C, 81.45; H, 9.06; N, 9.50. Found: C, 81.35; H, 9.09; N, 9.57.
	In N,N-dimethyl-formamide; at 85℃; for 4h;Inert atmosphere;	(1) 0.3mmol compound of formula II is dissolved in 15 ml of anhydrous dimethylformamide (DMF), under a nitrogen atmosphere, added the 1.2mmol of piperazine to the above solution, stirred at 85 C for 4 hours, and then the mixture is cooled at room temperature. The solvent has been removed by distillation under reduced pressure; the distillation residue is purified by silica gel column chromatography under reduced pressure, the eluent is a mixture of dichloromethane and methanol with a volume ratio of 40: 1, and then obtained compound of formula III

Reference： [1]Dyes and Pigments,2013,vol. 99,p. 903 - 907
[2]Patent: CN106588906,2017,A .Location in patent: Paragraph 0044; 0045

40
[ 25560-00-3 ]
[ 207399-07-3 ]
[ 1313374-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 0.666667h;

Reference： [1]Samanta, Animesh; Vendrell, Marc; Yun, Seong-Wook; Guan, Zhenping; Xu, Qing-Hua; Chang, Young-Tae [Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1353 - 1357]

41
[ 207399-07-3 ]
[ 1377297-20-5 ]
2-((E)-2-((E)-2-((19-((2-carbamoyl-5-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazol-1-yl)phenyl)amino)-4,7,10,13,16-pentaoxanonadecyl)amino)-3-((E)-2-(3,3-dimethyl-1-propylindolin-2-ylidene)ethylidene)cyclohex-1-en-1-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-ium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With N-ethyl-N,N-diisopropylamine; In ethanol; dimethyl sulfoxide; at 70℃; for 3h;	2-((E)-2-((E)-2-((19-((2-carbamoyl-5-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-lH- indazol-l-yl)phenyl)amino)-4,7,10,13,16-pentaoxanonadecyl)amino)-3-((E)-2-(3,3- dimethyl-l-propylindolin-2-ylidene)ethylidene)cyclohex-l-en-l-yl)vinyl)-3,3-dimethyl-l- [00233] Amine 8 (12.1 mg, 20 μιηο) was dissolved in DMSO (200 L) and added to <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (7 mg, 10 μιηο) and treated with Hunig's base (15 μ) followed by ethanol (100 μ). The sample was heated for 3 h at 70 C. The entire sample was added to a silica gel column (2.5 x 20 cm) and chromatographed with CH2C12 (200 mL), CH2Cl2/MeOH/NH3 39/0.9/0.1 (240 mL), 19/0.9/0.1 (240 mL) and 12.3/0.9/0.1 (240 mL). The blue band was concentrated to give product 14 (2.4 mg, 22%) as a blue solid. MS (ESI): m/z 554.1 [M+H]2+.

Reference： [1]Patent: WO2014/25395,2014,A1 .Location in patent: Paragraph 00233

42
[ 207399-07-3 ]
[ 1563057-62-4 ]
[ 1563057-66-8 ]

Yield	Reaction Conditions	Operation in experiment
16%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 16h;Inert atmosphere;	CS788 To a mixture of NaH (60% oil dispersion, 4.0 mg, 94 mmol) and compound 6 (38 mg, 94 mmol) in DMF (5 mL) was added <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (52 mg, 78 mmol). After stirring at room temperature for 16 h, the reaction mixture was diluted with a mixture of AcOEt-toluene (3:1, 30 mL), and then washed with water (10 mL×5) and brine (10 mL). The organic layer was dried over Na2SO4 and then evaporated. Purification by column chromatography (MeOH-dichloromethane, 1:20) afforded CS-788 as a green film (13 mg, 16%). 1H-NMR (CDCl3, 400 MHz): δ 7.93 (2H, d, J=14.2 Hz), 7.33 (2H, t, J=7.4 Hz), 7.27 (2H, d, J=6.2 Hz), 7.18 (2H, t, J=7.4 Hz), 7.09 (2H, d, J=8.0 Hz), 6.97 (2H, d, J=9.1 Hz), 6.68 (2H, d, J=9.1 Hz), 6.07 (2H, d, J=14.2 Hz), 4.07 (4H, t, J=7.2 Hz), 3.47 (4H, t, J=7.0 Hz), 2.75-2.65 (16H, m), 2.55 (4H, q, J=7.4 Hz), 2.04 (2H, m), 1.85 (4H, m), 1.38 (12H, s), 1.22 (6H, t, J=7.4 Hz), 1.05 (6H, t, J=7.5 Hz). 13C-NMR (CDCl3, 100 MHz): δ 171.7, 165.0, 152.7, 142.3, 142.2, 142.1, 140.9, 128.6, 124.9, 122.8, 122.1, 115.6, 14.7, 110.6, 100.0, 52.3, 48.9, 46.1, 32.5, 31.8, 29.6, 27.9, 26.1, 24.6, 20.8, 14.8, 11.7. LRMS (ESI): calculated for [(M-I)+] 908.5. found 908.5. HRMS (ESI): calculated for C54H7401N3S4 [(M-I)+] 908.4709. found 908.4740.

Reference： [1]Patent: US2014/51863,2014,A1 .Location in patent: Paragraph 0204; 0236; 0247-0248

43
[ 207399-07-3 ]
[ 1849-36-1 ]
C₄₂H₄₈N₃O₂S⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 8360 - 8364

44
[ 110-85-0 ]
[ 207399-07-3 ]
[ 1477522-55-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	In N,N-dimethyl-formamide; at 85℃; for 4h;Inert atmosphere;	The specific synthesis steps are as follows: 1) Under inert anaerobic Condition , <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (0.5 mmol), Piperazine (2 mmol) and dried water-removed N, N-dimethylformamide were placed in a two-necked flask and reacted at 85 C for 4 hours. After the reaction was completed, Extract with CH2Cl2, dry the organic layer over anhydrous Na2SO4, The solvent was removed by rotary evaporation and the residue was separated by column chromatography The blue solid piperazine-substituted cyanine dye intermediate was obtained. Yield: 85%;
	In N,N-dimethyl-formamide; for 4h;Inert atmosphere;	After purging the two-necked 50ml flask with nitrogen three times, <strong>[207399-07-3]IR-780</strong> (300mg, 0.45mmol), piperazine (155mg, 1.8mmol) and 10mL double distilled DMF were added under nitrogen for 4 hours. At the end of this time, excess DMF was removed and the residue was separated by column chromatography to give a blue solid.
	In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; Darkness;	Cy7-Cl (668 mg, 1 mmol, 1 equiv.) was dissolved in anhydrous N,N-dimethylformamide (10 mL).Piperazine (345 mg, 4 mmol, 4 equiv.) was added under a nitrogen atmosphere.The mixed solution was stirred overnight at room temperature in the dark. Column chromatography (SiO2; CH2Cl2/CH3OH, 40:1, v/v)Purification gave a blue solid, Cy-NH.

Reference： [1]RSC Advances,2015,vol. 5,p. 85095 - 85104
[2]Molecular Pharmaceutics,2018,vol. 15,p. 3167 - 3176
[3]Journal of the American Chemical Society,2014,vol. 136,p. 5351 - 5358
[4]Patent: CN105038295,2017,B .Location in patent: Paragraph 0019-0023
[5]Biomedicine and Pharmacotherapy,2019,vol. 116
[6]Dyes and Pigments,2017,vol. 143,p. 245 - 251
[7]Patent: CN105001161,2018,B .Location in patent: Paragraph 0046 - 0051
[8]Patent: CN108440369,2018,A .Location in patent: Paragraph 0033; 0035; 0038; 0043; 0048; 0053

45
[ 109-83-1 ]
[ 207399-07-3 ]
C₃₉H₅₂N₃O⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In acetonitrile; at 70℃; for 2h;Sealed tube;	To a solution of <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> 3 (100 mg, 0.150 mmol) in methyl cyanide (MeCN, 5 mL) was added N-methylethanolamine 7 (60 0.750 mmol). The solution was heated to 70 C in a sealed vial for 2 hours as the reaction color transitioned from green to dark blue. After this time LC/MS analysis showed complete consumption of 3. The reaction mixture was concentrated in vacuo, and the residue was purified by silica gel chromatography (100% EtOAc, then 0→10% MeOH/DCM) afforded 6 (85 mg, 80%) as a dark blue iridescent solid. Compound 6 had a broad hypsochromic absorbance with a maximum at 687 nm. 1H NMR (CDC13, 400 MHz) δ 7.69 (d, J = 13.0 Hz, 2H), 7.30 (t, J = 1.5 Hz, 4H), 7.09 (d, J = 1.5 Hz, 2H), 6.89 (d, J = 1.9 Hz, 2H), 5.69 (d, J = 13.03 Hz, 2H), 4.12 - 3.94 (m, 4H), 3.81 (t, J = 7.4 Hz, 4H), 3.55 (s, 3H), 2.47 (t, J = 6.6 Hz, 4H), 1.90 - 1.76 (m, 6H), 1.67 (s, 12H), 1.04 (t, J = 1.4 Hz, 6H); 13C NMR (CDCI3, 100 MHz) δ 176.9, 168.5, 143.0, 142.2, 140.5, 128.1, 123.5, 123.0, 122.2, 108.7, 95.0, 60.0, 59.3, 48.1, 45.3, 44.9, 29.4, 24.9, 21.9, 20.2, 11.7; IR (thin film) 1544, 1509, 1444, 1345 cm"1; HRMS (ESI) calculated for C39H52N3O (M+) 578.4110, observed 578.4096.

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 14153 - 14159
[2]Patent: WO2016/72984,2016,A1 .Location in patent: Page/Page column 28

46
[ 207399-07-3 ]
C₄₂H₅₆N₃O₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Patent: WO2016/72984,2016,A1
[2]Organic Letters,2015,vol. 17,p. 302 - 305

47
[ 42055-15-2 ]
[ 207399-07-3 ]
C₄₀H₅₄N₃O⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In acetonitrile; at 80℃; for 0.166667h;Sealed tube;	To a solution of IR-780 iodide 3 (315 mg, 0.472 mmol) in MeCN (3 mL) was added 3-methylamino-l-propanol (230 mu, 2.36 mmol). The solution was heated to 80 C in a sealed vial for 10 minutes as the reaction color transitioned from green to dark blue. After this time LC/MS analysis showed complete consumption of 3. The reaction mixture was concentrated in vacuo, and the residue was purified by silica gel chromatography (0?10% MeOH/DCM) to afford 18 (285 mg, 84%) as a dark blue iridescent solid. 1H NMR (CD3CN, 400 MHz) delta 7.51 (d, J = 13.3 Hz, 2H), 7.38 (d, J = 7.3 Hz, 2H), 7.33 - 7.25 (m, 2H), 7.13 - 7.03 (m, 4H), 5.83 (d, J = 13.4 Hz, 2H), 3.86 (m, 6H), 3.55 (q, J = 5.6 Hz, 2H), 3.40 (s, 3H), 3.02 (t, J = 4.9 Hz, 1H), 2.47 (t, J = 6.6 Hz, 4H), 2.01 - 1.93 (m, 2H), 1.83 - 1.69 (m, 6H), 1.59 (s, 12H), 0.98 (t, J = 7.4 Hz, 6H); 13C NMR (CD3CN, 125 MHz) delta 176.8, 169.4, 144.2, 142.2, 141.3, 129.1, 124.3, 123.8, 122.9, 110.3, 95.9, 59.6, 56.8, 48.6, 45.7, 45.4, 32.5, 29.4, 25.4, 22.6, 20.8, 11.6; IR (thin film) 3339, 1540, 1508, 1449, 1344, 1256 cm"1; HRMS (ESI) calculated for C4oH54N30 (M+) 592.4261, observed 592.4255.

Reference： [1]Organic Letters,2015,vol. 17,p. 302 - 305
[2]Patent: WO2016/72984,2016,A1 .Location in patent: Page/Page column 39

48
[ 207399-07-3 ]
[ 74654-07-2 ]
C₄₃H₆₀N₃O₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 6948 - 6951

49
[ 207399-07-3 ]
[ 94564-78-0 ]
C₃₃H₃₉N₂O₃⁽¹⁺⁾ [ No CAS ]

Reference： [1]Analytical Chemistry,2020,vol. 92,p. 5772 - 5779
[2]Angewandte Chemie - International Edition,2014,vol. 53,p. 10916 - 10920
Angew. Chem.,2014,vol. 126,p. 11096 - 11100,5

50
[ 207399-07-3 ]
[ 1074-36-8 ]
C₄₃H₄₉N₂O₂S⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Macromolecular Bioscience,2016,p. 1432 - 1441
[2]Journal of Materials Chemistry B,2015,vol. 3,p. 8321 - 8327

51
[ 207399-07-3 ]
[ 22948-02-3 ]
C₄₂H₅₀N₃S⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In N,N-dimethyl-formamide; at 25℃; for 10h;Inert atmosphere; Schlenk technique;	A mixture of compounds <strong>[207399-07-3]IR-780</strong> (333.65mg, 0.5mmol) and 4-amino thiophenol (69mg, 0.55mmol) were stirred in DMF (5mL) for 10h under an argon atmosphere at 25C. After completion of present reaction, the solvent was removed under reduced pressure. The crude mixture was purified by flash chromatography on silica gel using dichloromethane/methanol (60: 1) to give 3 (223mg, 60%).1H NMR (400MHz, CDCl3): δ ppm=1.06 (t, J=16Hz, 6H, CH3), 1.52 (s, 12H, CH3), 1.91 (q, 4H, CH2), 2.04 (t, J=12Hz, 2H, CH2), 2.78 (t, J=12Hz, 4H, CH2), 4.09 (t, J=16Hz, 4H, CH2), 6.19 (d, J=16Hz, 2H, CH2=CH-H), 6.56 (s, 1H, Ar-H), 6.63 (d, J=12Hz, 2H, Ar-H), 6.99 (q, 1H, Ar-H), 7.10 (d, J=8Hz, 2H, Ar-H). 7.19 (t, J=16Hz, 3H, Ar-H). 7.32 (t, J=20Hz, 5H, Ar-H), 8.68 (d, J=12Hz, 2H, CH2=CH-H).

Reference： [1]Dyes and Pigments,2016,vol. 131,p. 84 - 90

52
[ 207399-07-3 ]
[ 108-98-5 ]
IR-792 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In N,N-dimethyl-formamide; at 25℃; for 10h;Inert atmosphere; Schlenk technique;	A mixture of compounds <strong>[207399-07-3]IR-780</strong> (333.65mg, 0.5mmol) and thiophenol (60.6mg, 0.55mmol) were stirred in DMF (5mL) for 10h under an argon atmosphere at 25C. After completion of present reaction, the solvent was removed under reduced pressure. The crude mixture was purified by flash chromatography on silica gel using dichloromethane/methanol (60: 1) to give 1 (330mg, 87%).1H NMR (400MHz, CDCl3): δ ppm=1.06 (t, J=12Hz, 6H, CH3), 1.48 (s, 12H, CH3), 1.89 (q, 4H, CH2), 2.06 (t, J=12Hz, 2H, CH2), 2.79 (t, J=12Hz, 4H, CH2), 4.13 (t, J=12Hz, 4H, CH2), 6.22 (d, J=12Hz, 2H, CH2=CH-H), 7.08 (t, J=16Hz, 1H, Ar-H), 7.12 (d, J=8Hz, 2H, Ar-H), 7.28 (d, J=8Hz, 3H, Ar-H), 7.36 (t, J=16Hz, 2H, Ar-H), 8.66 (d, J=12Hz, 2H, CH2=CH-H).

Reference： [1]Dyes and Pigments,2016,vol. 131,p. 84 - 90

53
[ 207399-07-3 ]
[ 1193-02-8 ]
C₄₂H₅₀N₃S⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.4%	In N,N-dimethyl-formamide; at 20℃;	The main process for chemical synthesis in thisexample was shown in FIG. 2. The synthesis steps were asfollows. IR780 iodide (2-[2-[2-Chloro-3-(1,3-dihydro-3,3-dimethyl-1-propyl-2H -indol-2-ylidene) ethylidene ]-1-cyclohexen-1-yl]etheny 1]-3,3 -dimethy 1-1-propy lindoliumiodide) (120 mg, 143.2 flillOl) and 4-aminothiophenol (300mg, 958 flillOl) were dissolved in anhydrous DMF (5 ml),and reacted overnight at room temperature. The obtainedcrude product was purified by preparative HPLC coupledwith a C-18 colunm, to obtain a pure target product IR780-NH2. A green solid (120 mg, 79.4%) was obtained afterdrying, which was then analyzed by HPLC, and identified bynuclear magnetic resonance spectrometry and mass spectrometry.IR780-NH2 (75.5 mg, 100 f.tmol) was dissolved inanhydrous DMF (5 ml), and triethyl amine (20 mg, 200f.tmol) was added. Then, a solution ofDOTA-NHS (153 mg,200 flillOl) dissolved in DMF (1 ml) was added to thereaction mixture, and stirred for 3 days at room temperature.The obtained crude product was purified by preparativeHPLC coupled with a C-18 colunm using, as a mobile phase,60% CAN and 40% H20 containing 0.1% TFA which wasgradient to 100% ACN in 15 min, to obtain a pure targetproduct. A green solid (21 mg, 17.2%) was obtained afterdrying, and the structure of the multi-functional probe of thepresent invention was determined after analysis by HPLCand identification by nuclear magnetic resonance spectrometryand mass spectrometry.
75%	In N,N-dimethyl-formamide; at 25℃; for 10h;Inert atmosphere; Schlenk technique;	A mixture of compounds <strong>[207399-07-3]IR-780</strong> (333.65mg, 0.5mmol) and 4-amino thiophenol (69mg, 0.55mmol) were stirred in DMF (5mL) for 10h under an argon atmosphere at 25C. After completion of present reaction, the solvent was removed under reduced pressure. The crude mixture was purified by flash chromatography on silica gel using dichloromethane/methanol (60: 1) to give 2 (278mg, 75%).1H NMR (400MHz, CDCl3): δ ppm=1.06 (t, J=16Hz, 6H, CH3), 1.56 (s, 12H, CH3), 1.89 (q, 4H, CH2), 2.00 (t, J=12Hz, 2H, CH2), 2.71 (t, J=12Hz, 4H, CH2), 4.08 (t, J=16Hz, 4H, CH2), 6.14 (d, J=16Hz, 2H, CH2=CH-H), 6.64 (d, J=8Hz, 2H, Ar-H), 7.00 (d, J=12Hz, 2H, Ar-H), 7.11 (d, J=8Hz, 2H, Ar-H), 7.21 (t, J=12Hz, 3H, Ar-H). 7.31 (d, 1H, Ar-H). 7.33 (d, J=4Hz, 2H, Ar-H). 7.36 (d, J=8Hz, 2H, Ar-H). 8.74 (d, J=16Hz, 2H, CH2=CH-H).

Reference： [1]Patent: US2019/71429,2019,A1 .Location in patent: Paragraph 0042-0043
[2]Dyes and Pigments,2016,vol. 131,p. 84 - 90

54
[ 207399-07-3 ]
2,6-bis(2-(3,3-dimethyl-1-propyl-1,3-dihydro-2H-indolin-2-ylidene)ethylidene)cyclohexanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium acetate; In N,N-dimethyl-formamide; at 80℃; for 6h;	IR780 (1 g, 1.5 mmol) and 2 g of sodium acetate were dissolved in 20 ml of DMF and reacted at 80 C for 6 hours.The reaction solution was extracted with ethyl acetate and washed with water three times.Dichloromethane / methanol = 20: 1 as the eluent passed through the column to give 600mgRed solid metal I-2 with a metallic luster, yield 60%.

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12368 - 12374
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 6350 - 6357
[3]Patent: CN108641710,2019,B .Location in patent: Paragraph 0036-0039

55
[ 83578-21-6 ]
[ 207399-07-3 ]
C₄₃H₅₃N₄S₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 2h;Reflux;	CD123 antibody probe conjugates were synthesized as fluorescent probes for in vitro cellular uptake studies. <strong>[207399-07-3]IR-780</strong> dye was synthesized according to previously reported method.26 Then <strong>[207399-07-3]IR-780</strong> dye was further modified with pyridyl disulfide reactive group. <strong>[207399-07-3]IR-780</strong> (51.0mg) and 4-(pyridin-2-yldisulfanyl)butanoic acid (30.0mg) were dissolved in acetonitrile. Then DIEA (27.0mg) was added and the resulting mixture was refluxed for 2h. The resulting mixture was condensed under vacuum. And intermediate 3 was purified to afford as a blue solid. The remaining procedures were similar with the synthesis of CD123-CPT.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5855 - 5860

56
[ 207399-07-3 ]
aluminium(III) sulfate hexahydrate [ No CAS ]
3C₃₈H₄₆ClN₂O₆S₂^(1-)*Al⁽³⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydroxide; In water;	As a cyanine dye, 1.00 g (1.33 mmol) of IR-783 iodide (manufactured by SIGMA-ALDRICH) was added to 50 g of water and 0.17 g of 16% NaOH aqueous solution (0.67 mmol of NaOH). Separately, 1.01 g (1.60 mmol) of aluminum sulfate hexahydrate (manufactured by SIGMA-ALDRICH) was added to 3 g of water to prepare an aqueous solution. The prepared aqueous solution was added dropwise. The formed precipitate was collected by filtration and washed with water. The obtained cake was dried to obtain 0.850 g (yield: 87%) of coloring material E represented by the following chemical formula (6).

Reference： [1]Patent: JP2015/48433,2015,A .Location in patent: Paragraph 0099; 0100

57
[ 207399-07-3 ]
tetrabutylphosphonium bis(1,3-dithiol-2-thione-4,5-dithiolato)nickel [ No CAS ]
C₃₆H₄₄ClN₂⁽¹⁺⁾*C₆NiS₁₀^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In 1,2-dichloro-ethane;	As a cyanine dye, 1.00 g (1.50 mmol) of <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (manufactured by SIGMA-ALDRICH) and tetrabutylphosphonium bis (1,3-dithiol-2-thione-4,5-dithiolato) nickel complex 1.07 g (1.50 mmol) were dissolved in 20 g of 1,2-ethylene dichloride. After shaking well with distilled water (20 ml) using a separating funnel, the aqueous layer was separated and discarded. This 1,2-ethylene dichloride layer was further washed twice with 20 ml of distilled water, and then granular anhydrous calcium chloride was added to the 1,2-ethylene dichloride layer for dehydration. After leaving it overnight, calcium chloride was filtered, the filtrate was concentrated with an evaporator, methanol was added to precipitate and crystallize the desired salt-forming dye, and the coloring material F represented by the following chemical formula (7) 1.13 g (yield 76%) was obtained.

Reference： [1]Patent: JP2015/48433,2015,A .Location in patent: Paragraph 0101; 0102

58
[ 207399-07-3 ]
phosphotungstic acid triacontahydrate [ No CAS ]
3C₃₆H₄₄ClN₂⁽¹⁺⁾*O₄₀PW₁₂^(3-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In ethanol; water;	A solution was prepared by adding 1.00 g (1.50 mmol) of <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (manufactured by SIGMA-ALDRICH, compound represented by the following chemical formula (1)) as a cyanine dye to 40 g of water and 160 g of ethanol. Separately, 1.62 g (0.47 mmol) of phosphotungstic acid n hydrate H 3 [PW 12 O 40] nH 2 O (n = 30) (manufactured by Nippon Biochemical Industries, Ltd.) as a polyacid was added to 40 g of water, Aqueous solution was prepared. The prepared polyacid aqueous solution was added dropwise to the dye solution. The formed precipitate was collected by filtration and washed with water. The obtained cake was dried to obtain 2.03 g (yield 93%) of coloring material A represented by the following chemical formula (2).

Reference： [1]Patent: JP2015/48433,2015,A .Location in patent: Paragraph 0090; 0092

59
[ 207399-07-3 ]
phosphotungstic acid triacontahydrate [ No CAS ]
phosphomolybdic acid triacontahydrate [ No CAS ]
0.5Mo₁₂O₄₀P^(3-)*3C₃₆H₄₄ClN₂⁽¹⁺⁾*0.5O₄₀PW₁₂^(3-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In ethanol; water;	As a cyanine dye, 1.00 g (1.50 mmol) of <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (manufactured by SIGMA-ALDRICH) was added to 40 g of water and 160 g of ethanol to prepare a solution. Apart from this, 0.81 g (0.24 mmol) of phosphotungstic acid · n hydrate H 3 [PW 12 O 40] · n H 2 O (n = 30) (manufactured by Nippon Biochemical Industries, Ltd.)0.56 g (0.24 mmol) of phosphomolybdic acid · n hydrate H 3 [PMo 12 O 40] · n H 2 O (n = 30) (manufactured by Nippon Biochemical Industries Co., Ltd.) was added to 40 g of water to prepare a polyacid aqueous solution. The prepared polyacid aqueous solution was added dropwise to the dye solution. The formed precipitate was collected by filtration and washed with water. The obtained cake was dried to obtain 1.81 g (yield 94%) of coloring material B represented by the following chemical formula (3).

Reference： [1]Patent: JP2015/48433,2015,A .Location in patent: Paragraph 0093; 0094

60
[ 207399-07-3 ]
phosphotungstic acid triacontahydrate [ No CAS ]
phosphomolybdic acid triacontahydrate [ No CAS ]
0.3Mo₁₂O₄₀P^(3-)*3C₃₆H₄₄ClN₂⁽¹⁺⁾*0.7O₄₀PW₁₂^(3-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In ethanol; water;	As a cyanine dye, 1.00 g (1.50 mmol) of <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (manufactured by SIGMA-ALDRICH) was added to 40 g of water and 160 g of ethanol to prepare a solution. Separately, 1.20 g (0.35 mmol) of phosphotungstic acid · n hydrate H 3 [PW 12 O 40] · n H 2 O (n = 30) (manufactured by Nippon Biochemical Industry Co., Ltd.) as a polyacid, phosphomolybdic acid · n water 0.36 g (0.15 mmol) of Japanese H3 [PMo 12 O 40] · n H 2 O (n = 30) (manufactured by Nippon Biochemical Industries Co., Ltd.) was added to 40 g of water to prepare a polyacid aqueous solution. The prepared polyacid aqueous solution was added dropwise to the dye solution. The formed precipitate was collected by filtration and washed with water. The obtained cake was dried to obtain 1.93 g (yield: 92%) of a color material C represented by the following chemical formula (4).

Reference： [1]Patent: JP2015/48433,2015,A .Location in patent: Paragraph 0095; 0096

61
[ 207399-07-3 ]
phosphomolybdic acid triacontahydrate [ No CAS ]
Mo₁₂O₄₀P^(3-)*3C₃₆H₄₄ClN₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In ethanol; water;	s a cyanine dye, 1.00 g (1.50 mmol) of <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (manufactured by SIGMA-ALDRICH) was added to 40 g of water and 160 g of ethanol to prepare a solution. Separately from this, 1.12 g (0.47 mmol) of phosphomolybdic acid n hydrate H 3 [PMo 12 O 40] nH 2 O (n = 30) (manufactured by Nippon Biochemical Industries, Ltd.) as a polyacid was placed in 40 g of water, Aqueous solution was prepared. The prepared polyacid aqueous solution was added dropwise to the dye solution. The formed precipitate was collected by filtration and washed with water. The obtained cake was dried to obtain 1.61 g (yield 96%) of color material D represented by the following chemical formula (5).

Reference： [1]Patent: JP2015/48433,2015,A .Location in patent: Paragraph 0097; 0098

62
[ 20205-29-2 ]
N-((2-chloro-3-((phenylimino)methyl)cyclohex-2-en-1-ylidene)methyl)aniline [ No CAS ]
[ 207399-07-3 ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium acetate; In ethanol; at 50℃; for 1h;	5.0 g (24.7 mmol, 2 eq) of the compound prepared in Step 1 of Preparation Example 3, 4.4 g (12.3 mmol, 1 eq) of the compound prepared in Step 3 of Preparation Example 1 and 2.6 g Eq) was dissolved in 20 mL of ethyl alcohol and reacted at 50 C for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature, concentrated under reduced pressure, and then crystals were formed with ethyl acetate, followed by filtration and drying under reduced pressure. (5.3 g, 79%).

Reference： [1]Patent: KR2015/49824,2015,A .Location in patent: Paragraph 0231; 0236-0238

63
[ 207399-07-3 ]
[ 501-97-3 ]
C₄₅H₅₃N₂O₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 5h;	500 mg (0.92 mmol, 1 eq) of the compound prepared in Step 2 of Preparation Example 3 was dissolved in 2.5 mL of DMF, 255.6 mg (1.85 mmol, 2 eq) of potassium carbonate and307.4 mg (1.85 mmol, 2 eq) of 3- (4-hydroxyphenyl) propionic acid was added and the mixture was stirred at 40 C for 5 hours. After completion of the reaction, 120 mL of ethyl acetate was added to form crystals, followed by filtration and drying under reduced pressure. Purification by silica gel column chromatography with chloroform: methyl alcohol (6: 1) yielded pure compound 7-3. (62.0 mg, 10%).

Reference： [1]Patent: KR2015/49824,2015,A .Location in patent: Paragraph 0231; 0240-0242

64
[ 207399-07-3 ]
[ 63545-55-1 ]
C₄₅H₅₃N₂O₂S⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 5h;	General procedure: 500 mg (0.92 mmol, 1 eq) of the compound prepared in Step 2 of Preparation Example 3 was dissolved in 2.5 mL of DMF, 255.6 mg (1.85 mmol, 2 eq) of potassium carbonate and307.4 mg (1.85 mmol, 2 eq) of 3- (4-hydroxyphenyl) propionic acid was added and the mixture was stirred at 40 C for 5 hours. After completion of the reaction, 120 mL of ethyl acetate was added to form crystals, followed by filtration and drying under reduced pressure. Purification by silica gel column chromatography with chloroform: methyl alcohol (6: 1) yielded pure compound 7-3. (62.0 mg, 10%). Except that 4-mercaptohydrocinnamic acid was used instead of 3- (4-hydroxyphenyl) propionic acid used in the Step 3 of Preparation Example 3 to obtain the title compound The desired compound was synthesized (710 mg, 18%).

Reference： [1]Patent: KR2015/49824,2015,A .Location in patent: Paragraph 0242; 0253-0255

65
[ 207399-07-3 ]
2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine [ No CAS ]
C₄₁H₄₇N₄O₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 254 - 258

66
[ 207399-07-3 ]
[ 351019-18-6 ]
C₄₁H₄₇FN₃⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 254 - 258

67
[ 207399-07-3 ]
[ 108-46-3 ]
hemicyanine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		Dissolve resorcinol (332 mg, 3.0 mmol) and K2CO3 (413 mg, 3.0 mmol)Solution to 20 mL of anhydrous acetonitrile under nitrogen The reaction was carried out at 35 C for 30 minutes.Then, a solution containing <strong>[207399-07-3]IR-780</strong> (1 g, 1.5 mmol) in acetonitrile was added to the mixture.The reaction was carried out for 4 h at 50 C, and the progress of TCL was detected.After the reaction,The solvent was evaporated in vacuo and the crude material was purified eluting elutObtained 0.41 g of Cy-OH as a dark green powdery product.The yield was 65%.
65%	With potassium carbonate; In acetonitrile; at 35 - 50℃; for 4.5h;Inert atmosphere;	Dissolve <strong>[207399-07-3]IR-780</strong> (1g, 1.5mmol) in 20ml of anhydrous acetonitrile to obtain solution D, dissolve resorcinol (332mg, 3.0mmol) and K2CO3 (413mg, 3.0mmol) In 20mL of anhydrous acetonitrile, under nitrogen, at 35 for 30 minutes to obtain solution E; then add solution D to solution E, react at 50 for 4 hours, TCL check the progress; after the completion of the reaction, vacuum evaporation The solvent and the crude product were purified by column chromatography (VDCM/VMeOH=40:1) to obtain a dark green powder product Cy-OH (0.41 g, yield 65%).

Reference： [1]Patent: CN109438426,2019,A .Location in patent: Paragraph 0021; 0039; 0042; 0044; 0045
[2]Patent: CN113527389,2021,A .Location in patent: Paragraph 0047; 0052-0052; 0056
[3]Dyes and Pigments,2017,vol. 143,p. 245 - 251
[4]RSC Advances,2021,vol. 11,p. 4356 - 4364

68
[ 207399-07-3 ]
[ 108-46-3 ]
C₂₈H₃₀NO₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]Patent: CN107383078,2017,A .Location in patent: Paragraph 0058; 0069; 0070; 0071; 0072; 0073-0078
[2]Chemical Communications,2017,vol. 53,p. 8759 - 8762
[3]Journal of Agricultural and Food Chemistry,2017,vol. 65,p. 9553 - 9558
[4]Journal of Agricultural and Food Chemistry,2019,vol. 67,p. 3062 - 3067

69
[ 207399-07-3 ]
[ 108-46-3 ]
(E)-2-(2-(6-hydroxy-2,3-dihydro-1H-xanthen-4-yl)vinyl)-3,3-di-methyl-1-propyl-3H-indol-1-ium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 50℃;Sealed tube;	Briefly, 15 mg (0.625 mmol) NaH (sodium hydride, 60% MW 24 g/mol) was placed in a flask under 0 C. Oxygen was removed and then replaced with argon and the device was sealed. 200 mg (1.816 mmol) resorcinol (C6H602 >99%, MW 110.11) was dissolved in 2 ml DMF (N, N-Dimethylformamide, C3H7NO) and then introduced to the flask via a syringe. 250 mg (0.375 mmol) IR780 (<strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong>, MW 667.11) was dissolved in 3 ml DMF and then introduced to the flask via syringe. The device was placed on a hot plate and the temperature was controlled at 50 C. After 3 hours, the system was cooled down to room temperature. The solution was poured to an ice-water mixture for precipitate. The crude product was filtered out for further purification via gel chromatography giving compound TMI as a blue solid (25 mg, yield 17%). Next, TMI (82 mg, 0.2 mmol) was dissolved in 5 mL dichloromethane, placed in a 4-drum vial covered with aluminum foil. NaBH4 (3 mg, 0.08 mmol in 0.5 mL methanol) was added drop-wise to the blue TMI solution, stirred for 10 min, generating a colorless solution. Distilled water was added to react with the excess NaBH4. The reaction mixture was then stirred for additional 10 min. The organic layer was then extracted with additional dichloromethane (5 mL x 2), dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to produce RTMI as an offyellow solid. TMI and RTMI were characterized by UV-vis, fluorescence, 1H MR, 13C NMR and MS. (0070) TMI 1H NMR (400 MHz, MeOD, Figs 3.1 and 3.2) δ 7.63 (d, J = 50.2 Hz, 1H), 6.97 (dd, J = 21.8, 9.5 Hz, 1H), 6.95 - 6.84 (m, 2H), 6.73 (d, J = 19.0 Hz, 1H), 6.64 (d, J = 7.5 Hz, 1H), 6.09 (s, 1H), 5.57 -5.40 (m, 1H), 5.33 (d, 1H), 3.05 - 2.84 (m, 2H), 2.44 - 2.26 (m, 4H), 1.65 (m, 2H), 1.62 (s, 6H), 1.4 (m, 2H), 0.90 (s, 3H). 13C NMR (101 MHz, MeOD, (Fig. 3.3)) δ 173.22 (s), 162.69 (s), 162.13 (s), 156.85 (s), 141.90 (s), 140.71 (s), 137.55 (s), 129.88 (s), 128.41 (s), 124.62 (s), 123.16 (s), 122.03 (s), 119.07 (s), 114.38 (s), 111.30 - 111.10 (m), 101.51 (s), 99.48 (s), 67.86 (s), 66.10 (s), 45.30 (s), 38.81 (s), 28.30 (s), 27.45 (s), 22.19 (s), 20.15 (s), 12.85 (s), 10.19 (s). LC/MS (positive mode), m/z, 412.6 for [M] + (0071) RTMI 1H NMR (400 MHz, MeOD, Figs. 3.5-3.7) δ 8.47 (d, J = 14.3 Hz, 1H), 8.13 - 7.86 (m, 1H), 7.62 (d, J = 10.9 Hz, 1H), 7.53 (m, 1H), 7.50 - 7.39 (m, 1H), 7.21 (dd, J = 31.9, 7.1 Hz, 1H), 6.67 (d, J = 8.7 Hz, 1H), 6.57 (d, J = 40.3 Hz, 1H), 6.12 (d, J = 14.3 Hz, 1H), 4.05 (t, J = 7.3 Hz, 1H), 2.63 (dt, J = 28.7, 5.9 Hz, 4H), 1.91 - 1.75 (m, 3H), 1.70 - 1.61 (m, 3H), 1.55 (d, J = 4.2 Hz, 1H), 0.84 - 0.75 (m, 3H). 13C NMR (101 MHz, MeOD) δ 158.56 (s), 154.06 (s), 150.43 (s), 146.19 (s), 138.73 (s), 130.97 (s), 128.65 (d, J = 36.1 Hz), 127.11 (dd, J = 119.1, 107.5 Hz), 121.23 (s), 119.38 - 118.61 (m), 117.24 (s), 114.22 (s), 108.71 (s), 106.66 - 105.72 (m), 78.81 - 77.11 (m), 66.29 (s), 43.80 (s), 38.81 (s), 33.36 (s), 30.20 (s), 28.72 (d, J = 4.8 Hz), 25.05 (s), 22.88 - 19.48 (m), 16.97 (s), 13.00 (s), 10.92 - 9.46 (m), 9.46 - 7.00 (m). LC/MS (positive mode), m/z: 414.6 for [M+H] +

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 1126 - 1134
[2]Patent: WO2017/62364,2017,A2 .Location in patent: Page/Page column 17-18

70
[ 20205-29-2 ]
N-((E)-(2-chloro-3-((E)-(phenylimino)methyl)cyclohex-2-enylidene)methyl)aniline [ No CAS ]
[ 207399-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In ethanol; at 120℃; for 0.333333h;Microwave irradiation;	General procedure: The near infrared cyanine dyes were prepared via a microwave assisted organic synthesis. The protocol for the synthesis has been discussed elsewhere [19,20,22]. The protocol was optimized using the Biotage single-mode microwave system. For each of the cyanine dyes, one equivalence of N-((E)-(2-chloro-3-((E)-(phenylimino)methyl)cyclohex-2-enylidene)methyl)aniline was made to react with 2 equivalence of the corresponding 2,3,3-trimethyl-1-R-3H-indolium iodide in the presence of sodium acetate and ethanol for 20 min at 120 C. Upon completion of each reaction, the product was cooled to 0 C, filtered, and washed with diethyl ether to obtain greenish-gold crystals with an average yield of 79%. The purified products were characterized using 1H and 13C NMR [19,20].

Reference： [1]Inorganica Chimica Acta,2017,vol. 467,p. 123 - 131

71
[ 207399-07-3 ]
[ 95-88-5 ]
C₂₈H₂₉ClNO₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 14778 - 14785

72
[ 207399-07-3 ]
C₂₆H₂₃N₃O₃ [ No CAS ]
C₆₂H₆₄N₅O₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With triethylamine; In acetonitrile; for 12h;Inert atmosphere; Reflux; Schlenk technique;	A suspension of compound N-Np (425 mg1.0 mmol) and Et3N (0.1 mL) in acetonitrile (15 mL each) was degassed with nitrogen for 15 min at room temperature. <strong>[207399-07-3]IR-780</strong> iodine (667 mg, 1.0 mmol) in acetonitrile (15 mL) that was degassed with nitrogen was added to the mixture with stirring. The mixture was stirred and refluxed under argon for 12 h, and then the versatile solvents were removed under reduced pressure. The residue was purified by column chromatography packed with silica gel using dichloromethane/methanol (20:1, v/v) as eluent to afford pure product N-CyNp as a blue solid. Yield: 170 mg, 18%.

Reference： [1]Chinese Chemical Letters,2017,vol. 28,p. 1979 - 1982

73
[ 207399-07-3 ]
[ 119301-59-6 ]
C₆₂H₆₃N₂O₄⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 1133 - 1136

74
[ 207399-07-3 ]
[ 554-84-7 ]
C₂₈H₃₁N₂O⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		The synthetic route is shown in Figure 1.In a 100 mL round bottom flask,3-nitrophenol (174 mg, 1.25 mmol)And sodium hydride (30.8 mg, 1.25 mmol)Dissolved in 6mL anhydrous DMF,Stir for 10 minutes at room temperature under nitrogen.Then, join by syringe<strong>[207399-07-3]IR-780</strong> (334 mg, 0.5 mmol),Stirring was continued for 12 hours at room temperature.Concentrated under reduced pressure,Dissolve the residue in CH2Cl2,Wash three times with deionized water,Dry anhydrous Na2SO4,Filter and concentrate,The resulting material was dissolved in 30 mL of methanol.Add SnCl2 (2g, 10mmol)And concentrated HCl (2 mL),The reaction solution was heated to 70 C and stirred overnight.Then, neutralized with saturated Na2CO3,The precipitate was removed by filtration and washed with CH2Cl2. The collected filtrate and washings were treated three times with water and dried over anhydrous Na2SO4. The solvent was removed by distillation under reduced pressure, the crude product with CH2Cl2 / CH3OH volume ratio of 50: 1 eluant is subjected to column chromatography to give a green solid product (144 mg, 70% yield), is the fluorescent probe.

Reference： [1]Patent: CN108219510,2018,A .Location in patent: Paragraph 0025; 0026; 0027

75
[ 207399-07-3 ]
[ 149505-94-2 ]
2-(2-{2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indol-2-ylidene)ethylidene]-2-(4-tert-butylcarbamate aminomethylphenoxy)-1-cyclohexen-1-yl}ethenyl)-3,3-dimethyl-1-propylindolium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With caesium carbonate; In dichloromethane; at 40℃; for 1h;Inert atmosphere;	Preparation of 2-(2-{2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indol-2-ylidene)ethylidene]-2-(4-tert-butylcarbamate aminomethylphenoxy)-1-cyclohexen-1-yl}ethenyl)-3,3-dimethyl-1-propylindolium iodide 6-2 A mixture of tert-butyl (4-hydroxyphenylmethyl)carbamate (348 mg, 1.5 mmol), <strong>[207399-07-3]IR-780</strong> (6-1) (500 mg, 0.75 mmol), and cesium carbonate (487 mg, 1.5 mmol) in anhydrous DCM (50 mL) was stirred at 40 C. under argon. After 1 h, the reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, eluted with DCM and MeOH) to yield the title product 6-2 (1.3 g, quant.).
100%	With caesium carbonate; In dichloromethane; at 40℃; for 1h;Inert atmosphere;	A mixture of tert-butyl (4-hydroxyphenylmethyl)carbamate (348 mg, 1.5 mmol), <strong>[207399-07-3]IR-780</strong> (6-1) (500 mg, 0.75 mmol), and cesium carbonate (487 mg, 1.5 mmol) in anhydrous DCM (50 mL) was stirred at 40 C. under argon. After 1 h, the reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, eluted with DCM and MeOH) to yield the title product 6-2 (1.3 g, quant.).

Reference： [1]Patent: US2018/179233,2018,A1 .Location in patent: Paragraph 0304; 0305
[2]Patent: US2020/383,2020,A1 .Location in patent: Paragraph 0503-0504

76
[ 207399-07-3 ]
C₃₆H₄₄N₅⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Science,2018,vol. 9,p. 7261 - 7270

77
[ 207399-07-3 ]
[ 554-84-7 ]
C₄₂H₄₈N₃O₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		m-Nitrophenol (7.61mmol, 1.059g) and NaH (7.61mmol, 0.304g) were dissolved in anhydrous DMF solution (80mL), and stirred at room temperature in Ar atmosphere for 10min. IR780 (3mmol, 2g) was dissolved in anhydrous DMF (10mL), and the above solution was slowly added dropwise with a syringe. The reaction was kept at room temperature and protected from light for 24 hours. The reaction was followed by mass spectrometry. The solvent was removed by rotary evaporation, and the silica gel column was purified. The developing solvent: CH2Cl2:CH3OH=50:1 (containing 2‰TEA), 1.4 g of green solid was obtained and the yield was about 60%.

Reference： [1]Patent: CN112745303,2021,A .Location in patent: Paragraph 0043-0046
[2]Analytical Chemistry,2018,vol. 90,p. 13759 - 13766

78
[ 207399-07-3 ]
[ 40327-96-6 ]
C₄₆H₆₅N₄⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.5%	In N,N-dimethyl-formamide; at 100℃; for 2h;Inert atmosphere;	Starting material C4 (1.32 g, 2 mmol), pentamethylpiperidine (0.34 g, 2 mmol)And 15mL DMF was added to a 50mL round bottom flask,Vacuuming and replacing N2 three times,The temperature was raised to 100 C for 2 hours. After cooling the reaction solution to room temperature,Concentrate the reaction solution in vacuo,Purified by silica gel column chromatography to give 1.24gBlue-black solid powder,The yield was 77.50%.

Reference： [1]Patent: CN109054428,2018,A .Location in patent: Paragraph 0076; 0087; 0088; 0089

79
[ 207399-07-3 ]
[ 94564-78-0 ]
C₃₃H₃₉N₂O₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With triethylamine; In N,N-dimethyl-formamide; at 50℃; for 4h;Inert atmosphere;	4-(morpholinemethyl)phenyl 1,3-diol (67 mg, 0.32 mmol) obtainedWith Et3N (5mg,0.064 mmol) dissolved in 20 mL DMF,After stirring for 10 min under N2 protection, IR 780 (106 mg, 0.16 mmol).The temperature was then raised to 50 C and the reaction was stirred for 4 h.After cooling,The reaction solution was evaporated to dryness under reduced pressure.Separating the obtained crude product by column chromatography (siliconGlue G, 200 to 300 mesh),Purification of CH2Cl2 / MeOH (v/v, 30:1) eluted to afford the product of the product, Lyso-pH (25 mg, 24%).

Reference： [1]Patent: CN104086536,2016,B .Location in patent: Paragraph 0082; 0085; 0086

80
[ 207399-07-3 ]
C₁₈H₁₈N₄O₂ [ No CAS ]
C₄₀H₄₂N₅O₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%		Compound 3, Scheme 2, (302 mg, 0.94 mmol) and K2CO3 (130 mg,0.94 mmol) were dissolved in acetonitrile (10 mL) in a 50 mL round-bottom flask. After the mixturewas stirred at room temperature under a N2 atmosphere for 15 min, a solution of <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (314 mg,0.47 mmol) in CH3CN (2.5 mL) was added to the mixture via a syringe, and the mixture was heated to 50 C for 5 h. When the solvent was removed under reduced pressure, the crude product was purifiedby silica gel chromatography using CH2Cl2/MeOH (15:1, v/v) as eluent, aording compound 4 as anaquamarine solid (160 mg, 55%). 1H NMR (400 MHz, CDCl3): 8.57-8.50 (m, 2H), 7.64-7.61 (m, 1H),7.42-7.38 (m, 2H), 7.31-7.27 (m, 3H), 7.17-7.14 (m, 2H), 7.10-7.03 (m, 3H), 6.86 (s, 1H), 6.67-6.63 (m,2H), 6.34-6.29 (m, 1H), 4.26 (s, 2H), 3.87-3.67 (m, 6H), 2.65 (s, 4H), 1.89-1.56 (m, 10H), 1.04-0.97 (s,3H); 13C NMR (100 MHz, CDCl3) 176.1, 163.4, 162.9, 157.9, 155.0, 149.4, 148.6, 145.0, 142.0, 141.5,137.6, 136.1, 130.0, 129.3, 126.8, 126.3, 123.8, 123.4, 122.8, 122.5, 115.2, 114.7, 112.4, 103.5, 102.7, 58.6, 55.9,53.7, 50.3, 47.2, 29.2, 28.6, 28.0, 24.7, 21.4, 20.6, 11.9. HRMS (ESI): calculated for C41H43N4O2+ [M]+:623.3381; found: 623.3629.

Reference： [1]Molecules,2019,vol. 24

81
[ 207399-07-3 ]
4-[Bis(2-pyridylmethyl)aminomethyl]-1,3-dihydroxylbenzene [ No CAS ]
C₄₁H₄₃N₄O₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		Compound 3, Scheme 2, (302 mg, 0.94 mmol) and K2CO3 (130 mg,0.94 mmol) were dissolved in acetonitrile (10 mL) in a 50 mL round-bottom flask. After the mixturewas stirred at room temperature under a N2 atmosphere for 15 min, a solution of <strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (314 mg,0.47 mmol) in CH3CN (2.5 mL) was added to the mixture via a syringe, and the mixture was heated to 50 C for 5 h. When the solvent was removed under reduced pressure, the crude product was purifiedby silica gel chromatography using CH2Cl2/MeOH (15:1, v/v) as eluent, aording compound 4 as anaquamarine solid (160 mg, 55%). 1H NMR (400 MHz, CDCl3): 8.57-8.50 (m, 2H), 7.64-7.61 (m, 1H),7.42-7.38 (m, 2H), 7.31-7.27 (m, 3H), 7.17-7.14 (m, 2H), 7.10-7.03 (m, 3H), 6.86 (s, 1H), 6.67-6.63 (m,2H), 6.34-6.29 (m, 1H), 4.26 (s, 2H), 3.87-3.67 (m, 6H), 2.65 (s, 4H), 1.89-1.56 (m, 10H), 1.04-0.97 (s,3H); 13C NMR (100 MHz, CDCl3) 176.1, 163.4, 162.9, 157.9, 155.0, 149.4, 148.6, 145.0, 142.0, 141.5,137.6, 136.1, 130.0, 129.3, 126.8, 126.3, 123.8, 123.4, 122.8, 122.5, 115.2, 114.7, 112.4, 103.5, 102.7, 58.6, 55.9,53.7, 50.3, 47.2, 29.2, 28.6, 28.0, 24.7, 21.4, 20.6, 11.9. HRMS (ESI): calculated for C41H43N4O2+ [M]+:623.3381; found: 623.3629.

Reference： [1]Molecules,2019,vol. 24

82
[ 2038-03-1 ]
[ 207399-07-3 ]
C₄₂H₅₇N₄O⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	In acetonitrile; at 50 - 80℃;Inert atmosphere;	IR780 and 4-(aminoethyl)-morpholine are dissolved in 50 to 100 mL of anhydrous acetonitrile in a ratio of 1:2, and reacted at 50 to 80 C for 6 to 10 hours under a N 2 atmosphere.After the reaction is cooled, the solvent is distilled off under reduced pressure;Step 2: The product obtained by evaporating the above solvent is passed through a silica gel column, and eluted with a gradient of methanol:methylene chloride from 0:100 to 1:20 to obtain L1, the yield is 15-20%.The melting point is 86.7 to 87.3 C.
15.2%	In acetonitrile; at 60℃;Inert atmosphere;	<strong>[207399-07-3]IR-780</strong> (0.0834 g,0.125 mmol) and 4-(2-aminoethyl)morpholine (0.0325 g,0.25 mmol) were dissolved in anhydrous MeCN(50 mL), then heated to 60 oC under N2 protection. After the reaction was completed, the reaction system was cooled to 25 oC, and concentrated under reduced pressure. The red solid (L1) was obtained by silica gel column chromatography with methanol/dichloromethane(v:v) from 0:100 to1:20. Yield 15.2%, m.p 86.7-87.3 oC; 1H NMR (DMSO-d6, 400 MHz), (ppm): δ 8.15 (s,1H), 7.59-7.62 (d,J 12.7 Hz,2H),7.46-7.48 (d,J 6.5 Hz,2H),7.27-7.31 (t, J 6.6 Hz, 2H), 7.15-7.17 (d,J 7.2 Hz,2H),7.06-7.07 (d,J 6.5 Hz,2H), 5.78-5.81 (d,J 12.4 Hz,1H),3.94 (s,4H), 3.80 (s,2H), 3.61 (s,4H), 2.64 (s,2H), 2.43(s, 2H), 1.70-1.73 (m, 6H),1.61 (s,12H),0.94-0.95 (d,J 6.3 Hz, 6H);13C NMR (DMSO-d6, 100 MHz), (ppm): δ 168.38,166.80,143.10,139.60,137.52,128.17, 122.38,122.12, 121.80,119.46,118.02,109.21, 94.32,73.70, 66.09,53.07,29.85,28.47,24.85,21.27,19.68,11.30. FT-IR (KBr,4000 -400 cm -1) : 3427,3129,2962,2926,1524,1485,1455,1399,1384,1345, 1319,1254, 1200, 1174, 1113,1051,1019, 924,800,716; HRMS (ESI-MS) Calcd for C42H57N4O[M] 633.4532, found 633.4533. L2 was synthesized in a similar manner from 4-(3-aminopropyl)morpholine. Red solid, yield 14.3%.m.p 90.1-91.2 oC. 1H NMR(DMSO-d6, 400 MHz), (ppm): δ 8.58 (s,1H),7.57-7.61 (d,J 12.8 Hz,2H),7.45-7.47 (d, J 7.2 Hz,2H), 7.27-7.31 (t, J 7.6 Hz,2H),7.15-7.17 (d, J 7.8 Hz, 2H), 7.03-7.07 (t, J 7.3 Hz,2H),5.77-5.80 (d,J 12.6 Hz,1H),3.93 (s,4H),3.77 (s,2H),3.55 (s,4H), 3.39(s,12H),2.35 (s,4H), 1.68-1.73 (dd, J 13.3, 6.5 Hz,6H), 1.60(s,12H),0.92-0.96 (t, J 7.3 Hz,6H); 13C NMR (DMSO-d6, 100 MHz), (ppm): δ 169.02,166.65, 143.12, 139.71,137.66,128.15,122.30,122.10,119.72,109.14, 94.23,66.12,47.13,28.43,24.95,21.32,19.67,11.31;FT-IR (KBr, 4000-400 cm -1):3428,3131,2961, 2926,2869, 2811,1525,1485,1455,1384,1290,1199,1172,1172,1114,1051,1019,919,800,716. HRMS (ESI-MS) Calcd for C43H60N4O[M] 647.4689, found 647.4682.

Reference： [1]Patent: CN109776380,2019,A .Location in patent: Paragraph 0052-0056
[2]Dyes and Pigments,2020,vol. 177

83
[ 207399-07-3 ]
C₁₂H₁₅BrN₂O₄ [ No CAS ]
C₄₈H₅₈BrN₄O₄⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 4h;Inert atmosphere;	Under argon protection,2g (3mmol) of <strong>[207399-07-3]IR-780</strong> was added to contain 1.5g (4.5mmol) of 1cAnd 0.62 g (4.5 mmol) of anhydrous potassium carbonate in 10 mL of anhydrous DMF,The reaction mixture was stirred at 40 C for 4 h.After the reaction, the reaction solution was diluted with 100 mL of ethyl acetate.And the aqueous washed twice with NaHCO3 saturated organic phase, the organic phase was dried over anhydrous sodium sulfate and ethyl acetate was removed under reduced pressure.Purified by column chromatography with methanol/dichloromethane (1:15) as eluent.The crude product was collected 1d as a green solid.Add 10 mL of trifluoroacetic acid to the dichloromethane solution containing the crude 1d.And stirred at 30 C for 2 h,The excess trifluoroacetic acid and dichloromethane are then removed under reduced pressure and purified by column chromatography.Using methanol/dichloromethane (1:15) as eluent,Compound 1 was obtained as a green solid 1.75 g, yield 60%.

Reference： [1]Patent: CN109776379,2019,A .Location in patent: Paragraph 0039; 0041; 0058-0060
[2]Chemical Communications,2019,vol. 55,p. 7374 - 7377

84
[ 207399-07-3 ]
C₁₂H₁₆N₂O₄ [ No CAS ]
C₄₈H₅₉N₄O₄⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Under argon protection,92 mg (2.3 mmol) of 60% sodium hydride was added to 2 mL of anhydrous DMF containing 568 mg (2.25 mmol) of 2c, and stirred at room temperature for 30 min.1 g of <strong>[207399-07-3]IR-780</strong> (1.5 mmol) was added and the mixture was warmed to 40 C and stirred overnight.After the reaction was completed, the reaction solution was diluted with 100 mL of ethyl acetate, and the organic phase was washed twice with saturated aqueous NaHCOs.The aqueous sodium sulfate was dried and the ethyl acetate was evaporated under reduced pressure. Purified by column chromatography eluting with methanol/dichloromethane (1:25)The crude product was collected in 2d as a green solid. Add 10 mL of trifluoroacetic acid to the dichloromethane solution containing the crude 2d.And stirred at 30 C for 2 h, then remove excess trifluoroacetic acid and dichloromethane under reduced pressure, and purified by column chromatography,Alcohol/dichloromethane (1:15) was used as the eluent to give compound 2 as a green solid, 0.71 g, yield 53%.

Reference： [1]Patent: CN109776379,2019,A .Location in patent: Paragraph 0039; 0041; 0061-0063
[2]Chemical Communications,2019,vol. 55,p. 7374 - 7377

85
[ 207399-07-3 ]
C₁₃H₁₈N₂O₅ [ No CAS ]
C₄₉H₆₁N₄O₅⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Under argon protection,92 mg (2.3 mmol) of 60% sodium hydride was added to 2 mL of anhydrous DMF containing 635 mg (2.25 mmol) of 3c.After stirring at room temperature for 30 min,1 g of <strong>[207399-07-3]IR-780</strong> (1.5 mmol) was added and the mixture was warmed to 40 C and stirred overnight.After the reaction was completed, the reaction solution was diluted with 100 mL of ethyl acetate.The organic phase was washed twice with a saturated aqueous solution of NaHCO3.The organic phase was dried over anhydrous sodiumPurification by column chromatography eluting with EtOAc/EtOAc (EtOAc:EtOAc)Add 10 mL of trifluoroacetic acid to a solution containing the crude 3d in dichloromethane.And stirred at 30 C for 2 h,The excess trifluoroacetic acid and dichloromethane are then removed under reduced pressure and purified by column chromatography.Using methanol/dichloromethane (1:15) as the eluent,Compound 3 was obtained as a green solid, 0.74 g, yield 58%.

Reference： [1]Patent: CN109776379,2019,A .Location in patent: Paragraph 0039; 0041; 0064-0065
[2]Chemical Communications,2019,vol. 55,p. 7374 - 7377

86
[ 207399-07-3 ]
[ 95-88-5 ]
C₂₈H₂₉ClNO₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%		4-chloro-resorcinol (140mg, 0.95mmol) and triethylamine (0.35mL, 2.4mmol) under an argon atmosphere at room temperature was dissolved to anhydrous DMF (1.5mL) and stirred for 30 min.<strong>[207399-07-3]<strong>[207399-07-3]IR-780</strong> iodide</strong> (250 mg, 0.375 mmol) was dissolved in dry DMF (1 mL) and slowly added to the above solution in the dark.Warm up to 50 degrees Celsius and keep warm for 4 hours.After cooling to room temperature, pure water (10 mL) was added and extracted with dichloromethane (20 mL×3).The organic phases were combined and the dichloromethane was evaporated under reduced pressure.The crude product was purified by preparative column chromatography (dichloromethane:ethanol = 30:1, v:v)The morphology was blue-green crystals (71 mg, 63%).

Reference： [1]Patent: CN109985006,2019,A .Location in patent: Paragraph 0074-0077

87
[ 207399-07-3 ]
[ 89996-01-0 ]
C₅₇H₆₆N₃P⁽²⁺⁾*I^(1-)*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 85℃; for 4h;Inert atmosphere;	Analytical balance accurately weighs a certain amount of IR780,It was dissolved in a mixed solvent of anhydrous N,N-dimethylformamide (DMF) and anhydrous dichloromethane, and placed in a double-necked flask.Weigh a certain amount of TPP-NH2 (References CJZhang, JGWang, JBZhang, YMLee, GXFeng, TKLim, HMShen, QSLin, B.Liu, Mechanism-guided design and synthesis of a mitochondria-targeting Artemisinin analoguewith enhanced anticancer activity, Angew.Chem.Int.Ed.2016,55,13770.Synthesis),Dissolved in DMF, added to the above stirred solution of IR780, and added triethylamine,The reaction was carried out under nitrogen at 85 C for 4 hours.The ratio of the substance of IR780:TPP-NH2:TEA is 1:2:4.After completion of the reaction, anhydrous DMF and methylene chloride were evaporated and evaporated.The crude product was dissolved in methanol, and the mixture was purified by silica gel column chromatographyThe elution procedure is 100:1→90:1→80:1→70:1→60:1→50:1→40:1→30:1→20:1→10:1,When the ratio becomes 10:1, the product is eluted.The pure product of T780 was obtained as a blue solid with a yield of 39%.

Reference： [1]Patent: CN110016048,2019,A .Location in patent: Paragraph 0035; 0054-0055

88
[ 207399-07-3 ]
[ 81744-01-6 ]
C₄₉H₅₂N₃O₂Se⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		(1) Take a 100ml three-necked flask, put magnets,Accurately weigh 0.5 mmol of 2- (4'-hydroxyphenyl) -1,2-benzoisoselenazole-3 (2H) -one,0.75 mmol of potassium tert-butoxide,Add another 15 ml of dry THF,Filled with nitrogen to replace and protect,And stirred under a nitrogen atmosphere at 15 C for 30 minutes to obtain a solution I. (2) Weigh 0.3 mmol of commercially available near-infrared fluorescent probe <strong>[207399-07-3]IR-780</strong> raw material (a heptachlorocyanine dye substituted with a median chlorine),Take 7.5 ml of solvent THF to dissolve to obtain solution II;Add solution II slowly to solution I,Slowly warm up to 60 ,Under nitrogen atmosphere, hold for 5h, then cool down,The solvent THF was removed under reduced pressure,A green solid was obtained and purified by silica gel column chromatography. The elution conditions were: ethyl acetate / methanol = 6/1,Collect green bands with a specific shift value (Rf value) of 0.2,0.12 g of a dark green solid was obtained with a yield of 92%.

Reference： [1]Patent: CN110330494,2019,A .Location in patent: Paragraph 0038-0048

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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere