[ CAS No. 23814-12-2 ] {[proInfo.proName]}

Name: 23814-12-2|1H-Benzo[d][1,2,3]triazole-5-carboxylic acid|97%
Brand: Ambeed
SKU: A194808
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3d Animation Molecule Structure of 23814-12-2

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Quality Control of [ 23814-12-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 23814-12-2 ]

SDS Specification

Alternatived Products of [ 23814-12-2 ]

Product Details of [ 23814-12-2 ]

CAS No. :	23814-12-2	MDL No. :	MFCD00012318
Formula :	C₇H₅N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	163.13	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 23814-12-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.85
TPSA :	78.87 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.24
Log Po/w (XLOGP3) :	0.62
Log Po/w (WLOGP) :	0.66
Log Po/w (MLOGP) :	0.64
Log Po/w (SILICOS-IT) :	0.89
Consensus Log Po/w :	0.61

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.73
Solubility :	3.03 mg/ml ; 0.0186 mol/l
Class :	Very soluble
Log S (Ali) :	-1.85
Solubility :	2.3 mg/ml ; 0.0141 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.9
Solubility :	2.04 mg/ml ; 0.0125 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.48

Safety of [ 23814-12-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 23814-12-2 ]

* 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 [ 23814-12-2 ]

[ 23814-12-2 ] Synthesis Path-Downstream 1~88

1
[ 136-85-6 ]
[ 23814-12-2 ]
[ 4546-95-6 ]

Reference： [1]Chemische Berichte,1893,vol. 26,p. 2736

2
[ 67-56-1 ]
[ 23814-12-2 ]
[ 113053-50-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 0 - 60℃; for 1h;	A suspension of compound 1 (CAS Reg. No. 23814-12-2; 1.8 g, 11.03 mmol) in MeOH (20 mL) was treated with thionyl chloride (2.416 mL, 33.1 mmol), added dropwise at 0 C. The reaction mixture was heated at 60 C. for 1 h, after which LCMS showed the reaction was complete. The solvent was evaporated using a rotary evaporator and the crude ester 2 was taken to the next step. LCMS ESI: calculated for C8H7N3O2=178.05 (M+H+); found: 178.0 (M+H+).

Reference： [1]Synthetic Communications,1993,vol. 23,p. 2019 - 2025
[2]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 336
[3]Patent: US2019/55243,2019,A1 .Location in patent: Paragraph 0131

3
[ 23814-12-2 ]
[ 108-24-7 ]
[ 264871-22-9 ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 3117 - 3123
[2]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 336

4
[ 23814-12-2 ]
[ 74-88-4 ]
5-carboxy-1,3-dimethyl-benzotriazolium; iodide [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 339

5
[ 23814-12-2 ]
[ 4546-95-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 336

6
[ 67-56-1 ]
3-carbamoyl-3H-benzotriazole-5-carboxylic acid [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

7
[ 64-17-5 ]
3-carbamoyl-3H-benzotriazole-5-carboxylic acid [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

8
3-carbamoyl-3H-benzotriazole-5-carboxylic acid [ No CAS ]
[ 64-19-7 ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

9
3-carbamoyl-3H-benzotriazole-5-carboxylic acid [ No CAS ]
[ 67-64-1 ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

10
[ 64-17-5 ]
1-carbamoyl-1H-benzotriazole-5-carboxylic acid [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

11
1-carbamoyl-1H-benzotriazole-5-carboxylic acid [ No CAS ]
furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

12
[ 411211-57-9 ]
[ 23814-12-2 ]

Reference： [1]Chemische Berichte,1882,vol. 15,p. 1882

13
4-nitro-3-ureido-benzoic acid [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Chemische Berichte,1882,vol. 15,p. 1882

14
[ 305-80-6 ]
[ 619-05-6 ]
[ 23814-12-2 ]

Reference： [1]Chemische Berichte,1882,vol. 15,p. 2189

15
[ 23814-12-2 ]
[ 64-17-5 ]
[ 73605-91-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sulfuric acid; at 90℃; for 8h;	To a solution of 1 H-benzo[d][1 ,2,3]triazole-5-carboxylic acid (5g, 0.O3mol) in ethanol (6OmL) was added sulphuric acid (7.35mL, 0.l3mol). The reaction mixture was stirred at 90C for 8 hours. The solvent was removed and the crude was basified until pH 7-8 then extracted with ethyl acetate. The organic layer was dried, filtered and the solvent was re-moved under reduced pressure giving the title compound as a white solid (5g, 85%), which was used in the next step without further purification.LRMS (mlz): 192 (M+1)+

Reference： [1]RSC Advances,2015,vol. 5,p. 82199 - 82207
[2]Synthetic Communications,1993,vol. 23,p. 2019 - 2025
[3]Patent: WO2014/95920,2014,A1 .Location in patent: Page/Page column 83

16
[ 23814-12-2 ]
[ 3082-95-9 ]
2,3,4-Tri-O-acetyl-1-O-(1H-benzotriazole-5-carbonyl)-D-glucopyranuronic acid methylester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1989,vol. 322,p. 457 - 459

17
[ 113053-50-2 ]
[ 67-56-1 ]
[ 23814-12-2 ]

Reference： [1]Archiv der Pharmazie,1989,vol. 322,p. 89 - 92

18
[ 113053-50-2 ]
[ 23814-12-2 ]
[ 132680-56-9 ]

Reference： [1]Archiv der Pharmazie,1990,vol. 323,p. 825 - 827

19
[ 120778-04-3 ]
[ 23814-12-2 ]
[ 67-63-0 ]

Reference： [1]Archiv der Pharmazie,1989,vol. 322,p. 89 - 92

20
[ 120778-03-2 ]
[ 71-23-8 ]
[ 23814-12-2 ]

Reference： [1]Archiv der Pharmazie,1989,vol. 322,p. 89 - 92

21
[ 120778-06-5 ]
[ 23814-12-2 ]
[ 78-92-2 ]

Reference： [1]Archiv der Pharmazie,1989,vol. 322,p. 89 - 92

22
[ 120778-07-6 ]
[ 23814-12-2 ]
[ 78-83-1 ]

Reference： [1]Archiv der Pharmazie,1989,vol. 322,p. 89 - 92

23
[ 120778-05-4 ]
[ 23814-12-2 ]
[ 71-36-3 ]

Reference： [1]Archiv der Pharmazie,1989,vol. 322,p. 89 - 92

24
[ 73605-91-1 ]
[ 23814-12-2 ]
[ 64-17-5 ]

Reference： [1]Archiv der Pharmazie,1989,vol. 322,p. 89 - 92

25
[ 23814-12-2 ]
[ 129295-49-4 ]
1H-Benzotriazole-5-carboxylic acid (1-benzyl-4-methyl-[1,4]diazepan-6-yl)-amide [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1912 - 1930

26
[ 23814-12-2 ]
[ 62-53-3 ]
1H-Benzotriazole-5-carboxylic acid phenylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1H-Benzotriazole-5-carboxylic acid phenylamide Benzotriazole-5-carboxylic acid (856 mg), HOAt (715 mg) and EDAC (1.00 g) were dissolved in DMF (17.5 mL) and the mixture was stirred at room temperature 1 hour. A 0.5 mL aliqot of this mixture was added to aniline (13.7 muL, 0.15 mmol) and the resulting mixture was vigorously shaken at room temperature for 16 hours. 1N hydrochloric acid (2 mL) and ethyl acetate (1 mL) were added and the mixture was vigorously shaken at room temperature for 2 hours. The organic phase was isolated and concentrated in vacuo to afford the title compound. HPLC-MS (Method B): m/z: 239 (M+1); Rt=3.93 min.
		Benzotriazole-5-carboxylic acid (856 mg), HOAt (715 mg) and EDAC (1.00 g) were dissolved in DMF (17.5 mL) and the mixture was stirred at room temperature 1 hour. A 0.5 mL aliqot of this mixture was added to aniline (13.7 muL, 0.15 mmol) and the resulting mixture was vigor¬ ously shaken at room temperature for 16 hours. 1N hydrochloric acid (2 mL) and ethyl ace¬ tate (1 mL) were added and the mixture was vigorously shaken at room temperature for 2 hours. The organic phase was isolated and concentrated in vacuo to afford the title com¬ pound.HPLC-MS (Method B): m/z: 239 (M+1); Rt = 3.93 min.
		Benzotriazole-5-carboxylic acid (856 mg), HOAt (715 mg) and EDAC (1.00 g) were dissolved in DMF (17.5 mL) and the mixture was stirred at room temperature 1 hour. A 0.5 mL aliqot of this mixture was added to aniline (13.7 muL, 0.15 mmol) and the resulting mixture was vigorously shaken at room temperature for 16 hours. 1N hydrochloric acid (2 mL) and ethyl acetate (1 mL) were added and the mixture was vigorously shaken at room temperature for 2 hours. The organic phase was isolated and concentrated in vacuo to afford the title compound. HPLC-MS (Method B): m/z: 239 (M+1); Rt=3.93 min.

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 6522 - 6523
[2]Patent: US2005/65066,2005,A1 .Location in patent: Page/Page column 40-41
[3]Patent: WO2006/5683,2006,A1 .Location in patent: Page/Page column 111-112
[4]Patent: US2003/229120,2003,A1 .Location in patent: Page 32-33

27
[ 23814-12-2 ]
[ 5720-05-8 ]
3-p-tolyl-3H-benzotriazole-5-carboxylic acid amide [ No CAS ]
1-p-tolyl-1H-benzotriazole-5-carboxylic acid amide [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 1623 - 1626

29
1-aminoformyl-benztriazole-carboxylic acid-⁽⁵⁾ [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

30
1-aminoformyl-benztriazole-carboxylic acid-⁽⁶⁾ [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

31
3.4-diamino-benzoic acid-hydrochloride [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Chemische Berichte,1869,vol. 2,p. 436
Chemische Berichte,1872,vol. 5,p. 201

32
[ 305-80-6 ]
3.4-diamino-benzoic acid-hydrochloride [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Chemische Berichte,1882,vol. 15,p. 2189

33
3-carbamoyl-3H-benzotriazole-5-carboxylic acid [ No CAS ]
[ 7664-41-7 ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

34
1-carbamoyl-1H-benzotriazole-5-carboxylic acid [ No CAS ]
[ 7664-41-7 ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

35
1-carbamoyl-1H-benzotriazole-5-carboxylic acid [ No CAS ]
[ 7732-18-5 ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

36
1-carbamoyl-1H-benzotriazole-5-carboxylic acid [ No CAS ]
[ 7732-18-5 ]
[ 64-19-7 ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

37
3-carbamoyl-3H-benzotriazole-5-carboxylic acid [ No CAS ]
alkaline solution [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

38
3-carbamoyl-3H-benzotriazole-5-carboxylic acid [ No CAS ]
natrium carbonate [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

39
1-carbamoyl-1H-benzotriazole-5-carboxylic acid [ No CAS ]
natrium carbonate [ No CAS ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 329,336,340

40
[ 23814-12-2 ]
permanganate [ No CAS ]
alkali [ No CAS ]
[ 4546-95-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 336

41
[ 136-85-6 ]
[ 7732-18-5 ]
potassium permanganate [ No CAS ]
alkali [ No CAS ]
[ 23814-12-2 ]
[ 4546-95-6 ]

Reference： [1]Chemische Berichte,1893,vol. 26,p. 2736

42
[ 7782-77-6 ]
[ 619-05-6 ]
[ 23814-12-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 336

43
4-nitro-3-ureido-benzoic acid [ No CAS ]
concentrated KOH-solution [ No CAS ]
[ 23814-12-2 ]
[ 15719-64-9 ]

Reference： [1]Chemische Berichte,1882,vol. 15,p. 1882

44
[ 23814-12-2 ]
[ 216014-70-9 ]
[ 337981-30-3 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 2197 - 2200

45
[ 23814-12-2 ]
7-nitro-1H-benzotriazole-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With nitric acid; In conc. sulphuric acid;	7-Nitro-<strong>[23814-12-2]1H-benzotriazole-5-carboxylic acid</strong> [21] 1H-Benzotriazole-5-carboxylic acid (1g, 6mmol) was dissolved in conc. sulphuric acid (20ml) and cooled to 0C on an ice bath. Nitric acid (20ml, excess) was added drop wise to the cooled solution over a period of 20 minutes. Stirring was continued for another 15 minutes at 0C and then at 90C for 2 hours, by which time TLC (A) indicated the conversion of starting material. The solution was cooled to room temperature and poured over ice to precipitate a white solid. The solid was collected by filtration and washed with copious amounts of water until neutral to afford [21] in 48% yield. Rf(A) 0.53; deltaH(400MHz; DMSO-d6) 8.77 (1H, s, BT) 9.01 (1H, s, BT) 13.75 (1H, br s, OH) 16.90 (1H, s, NH); m/z (EI-HR) 208.02288 [(M) calc. for C7H4N4O4 208.02325].

Reference： [1]Heterocycles,2002,vol. 57,p. 1461 - 1470
[2]Patent: EP1272827,2008,B1

46
[ 23814-12-2 ]
[ 109384-19-2 ]
3-(1-tert-butoxycarbonyl-piperidin-4-yl)-3H-benzotriazole-5-carboxylic acid [ No CAS ]
1-(1-tert-butoxycarbonyl-piperidin-4-yl)-1H-benzotriazole-5-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6921 - 6934

47
[ 23814-12-2 ]
[ 106429-67-8 ]

Yield	Reaction Conditions	Operation in experiment
16%		Example 240 : Synthesis of (1E,6E)-1-(1H-benzotriazol-5-yl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione (CU346); (1) Synthesis of 1H-benzotriazole-5-carboxaldehyde; To a solution of <strong>[23814-12-2]1H-benzotriazole-5-carboxylic acid</strong> (1.00 g, 6.13 mmol) in 30 mL of dry tetrahydrofuran was added lithium aluminum hydride (0.47 g, 12 mmol) under nitrogen at 0C. After the reaction mixture was stirred at 70C for 90 h, saturated Na2SO4 aqueous solution was added carefully at 0C. After the solution was stirred at room temperature for 30 min, a sufficient amount of Na2SO4 was added with additional stirring for drying. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (chloroform/methanol = 97/3 to 80/20) to obtain (1H-benzoimidazol-5-yl)methanol as a pale yellow solid (143 mg, 16%).

Reference： [1]Patent: EP2123637,2009,A1 .Location in patent: Page/Page column 65
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 5823 - 5836
[3]RSC Advances,2015,vol. 5,p. 82199 - 82207

48
[ 109-65-9 ]
[ 23814-12-2 ]
[ 120321-66-6 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1227 - 1230

49
[ 23814-12-2 ]
[ 7051-34-5 ]
1-(cyclopropylmethyl)-1H-benzotriazole-5-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1227 - 1230

50
[ 23814-12-2 ]
[ 106-95-6 ]
1-allyl-1H-benzotriazole-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ISOPROPYLAMIDE; at 60℃; for 18h;	Benzotriazole-5-carboxylic acid (0.163g, 1.0 MMOL), allyl bromide (0. 18g, 1.5 mmol) and potassium carbonate (0.304g, 2.2 mmol) were stirred for 18 hours at 60C in DMA (3 ML). The resulting solution was diluted with water and ACETONITRILE until all solid was dissolved, and purified by preparative HPLC to give 1-(allyl)-<strong>[23814-12-2]1H-benzotriazole-5-carboxylic acid</strong> m/z (ES+): 204 [M+H] +.'H NMR (CD30D) : 8.73 (s, 1H, C (4) -H), 8.19 (dd, 1H, JL=8. 8, J2=1.6, C (6)-H), 7.85 (d, 1H, J=8.4, C (7) -H), 6.1-6. 0 (m, 1H, CH=CH2), 5.50-5. 40 (m, 1H, CH=CHH trans to H), 5.35-5. 30 (m, 1H, CH=CHH cis to H), 4.90-4. 85 (m, 2H, NCH2).

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1227 - 1230
[2]Patent: WO2004/41274,2004,A1 .Location in patent: Page/Page column 62

51
[ 23814-12-2 ]
[ 918540-34-8 ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 3117 - 3123

52
[ 23814-12-2 ]
[ 132680-55-8 ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 3117 - 3123

53
[ 23814-12-2 ]
1H-benzotriazole-5-carbaldehyde oxime [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 5823 - 5836

54
[ 23814-12-2 ]
1-(1H-1,2,3-benzotriazol-5-yl)methanamine monohydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 5823 - 5836

55
[ 23814-12-2 ]
1-(1H-benzotriazol-5-ylmethyl)-3-(4-tert-butyl-benzyl)-thiourea [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 5823 - 5836

56
[ 23814-12-2 ]
[ 70938-42-0 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 5823 - 5836

57
[ 23814-12-2 ]
1-piperidin-4-yl-1H-benzotriazole-5-carboxylic acid; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6921 - 6934

58
[ 23814-12-2 ]
3-piperidin-4-yl-3H-benzotriazole-5-carboxylic acid; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6921 - 6934

59
[ 23814-12-2 ]
1-[(4-methoxy-phenyl)-diphenyl-methyl]-1H-benzotriazole-5-carboxylic acid (6-hydroxy-hexyl)-amide [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 2197 - 2200

60
[ 23814-12-2 ]
diisopropyl-phosphoramidous acid 2-cyano-ethyl ester 6-({1-[(4-methoxy-phenyl)-diphenyl-methyl]-1H-benzotriazole-5-carbonyl}-amino)-hexyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 2197 - 2200

61
[ 23814-12-2 ]
[ 337981-31-4 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 2197 - 2200

62
[ 23814-12-2 ]
permanganate [ No CAS ]
[ 106429-67-8 ]

Reference： [1]Synthetic Communications,1993,vol. 23,p. 2019 - 2025

63
[ 23814-12-2 ]
permanganate [ No CAS ]
[ 153915-05-0 ]

Reference： [1]Synthetic Communications,1993,vol. 23,p. 2019 - 2025

64
[ 23814-12-2 ]
permanganate [ No CAS ]
5-(benzotriazol-5-ylmethyl)-2,2,5-trimethyl-1,3-dioxane-4,6-dione [ No CAS ]

Reference： [1]Synthetic Communications,1993,vol. 23,p. 2019 - 2025

65
[ 23814-12-2 ]
permanganate [ No CAS ]
5,5-di-(benzotriazol-5-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione [ No CAS ]

Reference： [1]Synthetic Communications,1993,vol. 23,p. 2019 - 2025

66
[ 31252-42-3 ]
[ 23814-12-2 ]
4-benzylpiperidinyl-benzotriazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Using the procedure of Example 8, following are prepared

Reference： [1]Patent: US6340685,2002,B1 .Location in patent: Page column 23

67
[ 23814-12-2 ]
[ 29022-11-5 ]
[ 119831-72-0 ]
[ 76-05-1 ]
benzotriazol-5-ylcarbonyl-Gly₂-Arg₃-NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The compounds of the invention of general formula (12) can be prepared by means of stan- dard peptide chemistry (General procedure H), e. g. in 0.5 mmol scale, using Fmoc strategy and HOAt or HOBT activated amino acids. The compounds prepared in the following exam- ples according to General procedure (Q) were all isolated as the TFA salts. This procedure is further illustrated in the following: Typically, 2 gram of Fmoc Tentagel S RAM resin (Rapp Polymere, Tubingen) with substitu- tion 0,25 mmol/g was washed with NMP then treated with 25% piperidine in NMP for 30 min followed by wash with NMP which renders the resin ready for coupling. Step wise coupling OF FMOC-ARGININE (FMOC-ARG (PMC)-OH), FMOC-GLYCINE (FMOC-GLY-OH) and FMOC-4-AMINOBENZOIC ACID (FMOC-4-ABZ-OH) : To 2 mmol of Fmoc-L-Arg (Pmc) -OH (Novabiochem) was added 3,33 ml 0, 6M HOAt in NMP (Perseptives) or 0, 6M HOBT in NMP (Novabiochem) containing 0,2% BROMPHENOLBLUE as indicator and added 330 LL of diisopropylcarbodiimide DIC (Fluka) and the solution was then added to the resin. After coupling for minimum 1 hour, or when the blue colour disappeared, the resin was washed with NMP and the Fmoc group was deprotected with 25% piperidine in NMP for 20 minutes followed by wash with NMP. This stepwise assembling of the arginine residues was repeated to give 3,4, 5 or 6 arginines on the resin. The Fmoc-Glycine (No- vabiochem) and Fmoc-4-aminobenzoic acid (Fluka and Neosystems) were coupled using the same procedure as described for Fmoc-Arg (Pmc)-OH. Coupling OF A-OH, E. g. 1H-BENZOTRIAZOLE-5-CARBOXYLIC ACID on Gly. When A-OH, e. g. 1 H-BENZOTRIAZOLE-5-CARBOXYLIC acid (Aldrich) was coupled on a glycine or arginine residue the coupling procedure was as described above. Coupling of A-OH, e. g. 1H-BENZOTRIAZOLE-5-CARBOXYLIC ACID on Abz or 4-APAC : Due to the lower nucleophilicity of the amino group in Abz the following procedure was nec- essary. To 4 mmol of A-OH, e. g. 1 H-benzotriazole-5-carboxylic acid was added 6,66 ml of a solution of 0, 6M HOAt, 0,2 mmol dimethylaminopyridine (DMAP) and 4 mmol DIC and was then added to the resin and allowed to react overnight. Introduction OF FRAGMENT 4-APAC INSTEAD OF 4-ABZ : 4-Nitrophenoxyacetic acid may be coupled on a glycine or arginine residue using DIC and HOBT/HOAt as described above. Subsequent reduction of the nitro group may be done us- ing SNCI2 in NMP or DMF e. g. as described by TUMELTY et al. (Tet Lett., (1998) 7467-70). Cleavage of the peptides from the resin. After synthesis the resin was washed extensively with diethyl ether and dried. To 1 gram* of the peptidyl resin was added 25 ml of a TFA solution containing 5% thioanisole, 5% ethanol, 5% phenol and 2% triisopropylsilane and allowed to react for 2 hours. The TFA solution was filtered and concentrated with argon flow for approximately 30 minutes. Then diethylether ca. 5-7 times the residual volume of TFA was added and the peptide precipitate was extracted in 10% ACOH and washed 5 times with diethyl ether and LYOPHILIZED. RP-HPLC analysis and purification : The crude products were analysed on RP-HPLC C18 column (4,6 x 250 mm) using one of two gradients (see table 1 and 2), temperature 25C, wavelength 214 nm and flow rate 1 ml/min with A-buffer 0,15 % TFA in H20 and B- Buffer (87,5 % (W/W) MeCN, 0,13 % (w/w) TFA in H2O). The products were purified on preparative RP-HPLC C18 column (2x25 cm) using a gradient (variable, see e. g example 1013 and similar), temperature 25C, wavelength 214 nm and flow rate 6 ML/MIN with A-buffer 0, 15 % (W/W) TFA in H20 and B-Buffer (87,5 % (W/W) MECN, 0, 13 % (w/w) TFA in H2O) and verified by mass spectrometry (MALI). Table 1 : Time (min.) Flow (ml/min) %A %B ( 0 1,00 95,0 5,0 30, 00 1, 00 80, 0 20, 0 35,00 1,00 0,0 100,0 40, 00 1,00 0,0 100,0 45, 00 1, 00 95, 0 5, 0 Table 2: Time (min.) Flow (ml/min) % A % B 0 1, 00 95, 0 5, 0 30, 00 1, 00 40, 0 60, 0 31, 00 1, 00 0, 00 100, 0 35, 00 10,00 0,00 100,0 36,00 1, 00 95, 0 5, 0 The following examples were prepared using this general procedure (O). Example 1010 (General Procedure (Q)) BENZOTRIAZOL-5-YLCARBONYL-GIY2-ARG3-NH2 (BT-G2R3). MS (MALDI) : m/z: 746.7 g/mol ; calculated : 744.2 g/mol. HPLC gradient: Time (min) Flow % A % B (ml/min) 0, 00 6, 00 90, 0 10, 0 120, 00 6,00 90,0 10,0 121, 00 0,10 90,0 10,0

Reference： [1]Patent: WO2004/80480,2004,A1 .Location in patent: Page/Page column 386-389

68
[ 23814-12-2 ]
1H-Benzotriazole-5-carboxylic acid phenylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Benzotriazole-5-carboxylic acid (856 mg), HOAT (715 mg) and EDAC (1.00 g) were dissolved in DMF (17.5 mL) and the mixture was stirred at room temperature 1 hour. A 0.5 mL aliqot of this mixture was added to aniline (13. 7, UL, 0.15 MMOL) and the resulting mixture was vigor- OUSLY shaken at room temperature for 16 hours. 1 N hydrochloric acid (2 mL) and ethyl ace- tate (1 mL) were added and the mixture was vigorously shaken at room temperature for 2 hours. The organic phase was isolated and concentrated in vacuo to afford the title com- pound. HPLC-MS (Method B): m/z: 239 (M+1); Rt = 3.93 min.

Reference： [1]Patent: WO2004/80480,2004,A1 .Location in patent: Page/Page column 108-109

69
(1R,2S)-2-[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride [ No CAS ]
[ 23814-12-2 ]
N-((1R,2S)-2-[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)-1H-1,2,3-benzotriazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With diethyl cyanophosphonate; triethylamine; In tetrahydrofuran; at 0 - 20℃; for 1h;	Example 219; N- ( ( 1R, 2 S ) -2- { [ ( 3 aR, 4R, 9bR) -4- (Methoxymethyl ) - 2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1- yl]carbonyl}cyclohexyl)-1H-1,2,3-benzotriazole-5- carboxamide; To a solution (5 ml) of (lR,2S)-2-[(3aR,4R,9bR)-4- (methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2- c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride (200 mg, 0.480 mmol) in THF were added triethylamine (0.199 ml, 1.44 mmol), 1H-1,2,3-benzotriazole-5- carboxylic acid (78.3 mg, 0.480 mmol) and DEPC (0.079 m 0.528 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgzS04, and concentrated under reduced pressur The obtained residue was subjected to column chromatography using silica gel and eluted with hexane: ethyl acetate (1: 1-1:9) to give the title compound (187 mg, 80%) as an amorphous form. ¹H-NMR (CDCl3) No.: 0. 86-0. 88 (lH, m), 1 .26 (lH, m), 1.43- 1.96 (10H, m) , 2.08-2.21 (2H, m), 2.41 (lH, m), 2.95 (1 m), 3.37-3.48 (3H, m), 3.58-3.76 (3H, m), 4.57 (lH, m), 5.66 (lH, d, J=6.9 Hz) , 6.53 (lH, d, J=7.3 Hz), 6.69 (1 dd, J=7.6,7.7 Hz), 7.03 (1H, dd, J=7.3, 7.6 Hz), 7.31- 7.34 (lH, m), 7.48 (lH, d, J=7.2 Hz), 7.66 (lH, d, J=7.(at) Hz), 8.17 (lH, s). LC/MS (ESI) m/z: 489 (MH(at)).

Reference： [1]Patent: WO2005/105802,2005,A1 .Location in patent: Page/Page column 237-238

70
[ 23814-12-2 ]
[ 875282-58-9 ]

Yield	Reaction Conditions	Operation in experiment
98%		Example 19; 4-Benzylpiperidine-l-carboxylic acid (lH-benzotriazol-5-carbonyI)-amide Fthe other tautomeric form of the compound is 4-benzylpiperidin-l-carboxylic acid (3H-benzotriazol-5-carbonyl)-amide1; 19a) lH-Benzotriazol-5-carboxylic acid amide (the other tautomeric form of the compound is 3H-benzotriazol-5-carboxylic acid amide)To a Suspension of 5.5 g (33.7 mmol) of benzotriazole-5-carboxylic acid [Aldrich] in 200 ml of dioxane 10 ml (137 mmol) of thionyl chloride and 0.5 ml dimethylformamide are added. The reaction mixture is stirred at room temperature overnight, then concentrated. The residue is gradually added to 50 ml of ammonium hydroxide at 0 C, then the reaction mixture is stirred at room temperature for l h and concentrated. The residue is purified by column chromatography using Kieselgel 60 aes adsorbent (Merck) and Chloroform : methanol = 4 : l aes eluent to yield 5.36 g (98 %) of the title compound. Mp.: 298-305 C .
	With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; N,N-dimethyl-formamide; at 20℃; for 2h;	To a solution of 1H-1,2,3-benzotriazole-5-carboxylic acid (2 g), EDCI/HCl (2.82 g), and HOBt in DMF (70 ml) was added an aqueous NH3 solution (5.1 ml), followed by reaction at room temperature for 2 hours. It was concentrated, and the residue was washed with a saturated NaHCO3 solution, collected by filtration, and dried to obtain 1H-1,2,3-henzotriazole-5-carboxamide (1.98 g) as a black solid.

Reference： [1]Patent: WO2006/10966,2006,A1 .Location in patent: Page/Page column 22
[2]Patent: EP2003132,2008,A1 .Location in patent: Page/Page column 28

71
(2S,4S)-1-[N-(2-amino-1,1-dimethylethyl)glycyl]-4-fluoropyrrolidine-2-carbonitrile dihydrochloride [ No CAS ]
[ 23814-12-2 ]
(2S,4S)-1-[[2-(1H-1,2,3-benzotriazol-5-yl)carbonylamino-1,1-dimethyl]ethylamino]acetyl-2-cyano-4-fluoropyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1H-1,2,3-Benzotriazole-5-carboxylic acid (57 mg) was dissolved in N,N-dimethylformamide (1.8 mL). To this solution, N,N'-carbonyldiimidazole (62 mg) was added at room temperature and stirred for 3 hours, followed by addition of (2S,4S)-1-[(2-amino-1,1-dimethyl)ethylamino]acetyl-2-cyano-4-fluoropyrrolidine dihydrochloride (100 mg). Triethylamine (133 muL) was then added under ice cooling and the reaction mixture was stirred for 10 minutes, warmed to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (developing solvent; chloroform:methanol:28% aqueous ammonia = 15:1:0.1 to 12:1:0.1 to 10:1:0.1) to give the titled compound (61 mg) as a light-yellow powder. 1H-NMR (300 MHz, DMSO-d6) delta 8.49-8.38 (2H, m), 7.99-7.82 (2H, m), 5.46 (1H, brd, J=51.0 Hz), 5.03-4.90 (1H, m), 3.97 (1H, dd, J=24.2, 12.7 Hz), 3.86-3.00 (5H), 2.64-2.25 (2H, m), 1.07 (6H, s).

Reference： [1]Patent: EP1627870,2006,A1 .Location in patent: Page/Page column 39

72
[ 23814-12-2 ]
[ 5329-14-6 ]
[ 24611-70-9 ]

Yield	Reaction Conditions	Operation in experiment
	With urea;	1H-Benzotriazole-5-carbonitrile 1H-Benzotriazole-5-carboxylic acid (1.0 g, 6.13 mmol), urea (0.552 g, 9.2 mmol) and sulfamic acid (1.19 g, 12.3 mmol) were heated to 240 C. for 1 h. The solid was triturated with water and the solid refluxed with CH2Cl2 for 1 h and the remaining solid removed by filtration. The solvent was removed to give 1H-benzotriazole-5-carbonitrile 100 mg (14%) as a white solid. 1H-NMR (CD3OD) delta: 7.77 (dd, J=1.2, 8.5 Hz, 1H), 8.02 (dd, J=1.2 Hz, 8.5 Hz, 1H), 8.48 (s, 1H); MS m/e 144 (MH+).

Reference： [1]Patent: US2003/207868,2003,A1

73
[ 102-09-0 ]
[ 23814-12-2 ]
[ 68-12-2 ]
[ 84902-17-0 ]

Yield	Reaction Conditions	Operation in experiment
98.0%	With sodium carbonate;	EXAMPLE 1 N,N-Dimethylformamide (200 g), <strong>[23814-12-2]1H-benzotriazole-5-carboxylic acid</strong> (100 g, 0.61 mole), diphenyl carbonate (157.58 g, 0.74 mole), and sodium carbonate (1.3 g, 0.012 mole) were mixed, heated to 100 C. and stirred at the same temperature for three hours. The resulting reaction mixture contained 143.7 g of 5-phenoxycarbonyl benzotriazole in a yield of 98.0%.

Reference： [1]Patent: US6548678,2003,B1

74
[ 23814-12-2 ]
[ 68-12-2 ]
[ 84902-17-0 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLES 2 to 14 N,N-Dimethylformamide (1.88 g), <strong>[23814-12-2]1H-benzotriazole-5-carboxylic acid</strong> (81.6 g, 0.5 mmole), and a metal oxide or a base (an organic or inorganic base) were mixed in an amount as indicated in Table 1, then heated to a temperature as indicated in Table 1 and stirred at the same temperature for five hours. Each of the resulting reaction mixture was analyzed on high-performance liquid chromatography, and the yield of 5-phenoxycarbonylbenzotriazole for each mixture was calculated. The results are in Table 1.

Reference： [1]Patent: US6548678,2003,B1

75
[ 23814-12-2 ]
[ 84902-17-0 ]

Yield	Reaction Conditions	Operation in experiment
		According to the present invention, 5-phenoxycarbonylbenzotriazole is produced from <strong>[23814-12-2]1H-benzotriazole-5-carboxylic acid</strong> in a relatively simple manner.

Reference： [1]Patent: US6548678,2003,B1

Yield	Reaction Conditions	Operation in experiment
94.4%		After cooling to 20 C., a solid product (46.15 parts, 94.4% yield) was isolated by filtration, washed with cold water (20 C.) and dried at 60 C. for 24 hours.

77
[ 23814-12-2 ]
[ 7664-93-9 ]
[ 125740-30-9 ]

Yield	Reaction Conditions	Operation in experiment
30.8%	With toluene-4-sulfonic acid; In hexane; ethyl acetate;	(B) Preparation of 5-allyloxycarbonyl benzotriazole 3.0 Parts of 5-carboxybenzotriazole (prepared as described in A) were added to a stirred mixture containing 50 parts of allyl alcohol and 0.2 parts of toluene-4-sulphonic acid. The reaction mixture was heated at the boil (94-97 C.) under reflux conditions for 24 hours. 0.3 Parts of concentrated sulphuric acid were then added and heating at the boil under reflux was continued for a further 48 hours. The excess allyl alcohol was removed by distillation under reduced pressure (20-25 Torr) and at 40-50 C. and the residual oil was dissolved in 100 parts of ethyl acetate. The ethyl acetate solution was washed with 100 parts of water, then dried over anhydrous magnesium sulphate. The ethyl acetate was then removed by distillation at 18-22 Torr and 50+-5 C., and the residual solid was stirred in 200 parts of hexane for four hours. The solid product (1.15 parts, melting point 95-97 C., 30.8% yield) was collected by filtration, washed with hexane and dried at 20-25 Torr and 20 C. for 16 hours. By analysis, the product was found to contain C 58.8% wt; N 20.1% wt; and H 4.6% wt. The compound 5-allyloxycarbonylbenzotriazole (C10 H9 N3 O2) requires C 59.1% wt; N 20.7% wt; and H 4.4% wt.

Reference： [1]Patent: US4978756,1990,A

78
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 23814-12-2 ]
Co₃(OH)2(1-benzotriazolide-5-carboxylato)2 * 3.7(H₂O) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 3456 - 3459

79
[ 23814-12-2 ]
[ 1512-02-3 ]
[ 1025027-06-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; at 70℃; for 48h;	To a mixture of 3.00 grams (5.1 mmol) of 12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19,19-heptadecafluoro-1-nonadecanol and 2.45 grams (15.0 mmol) of benzotriazole-5-carboxylic acid in 50 milliliters of a 9:1 mixture of tetrahydrofuran and dimethyl formamide were added 3.09 grams (15.0 mmol) of N,N-dicyclohexylcarbodiimide and 0.18 grams (1.5 mmol) of 4-(dimethylamino)pyridine, and the resultant mixture was heated at 70 C. for 48 h. The mixture was filtered, and the filtrate was concentrated to a dark tan solid. The crude product was slurried in 50 milliliters of tetrahydrofuran, the mixture was filtered, and the filtrate was concentrated to a tan solid. Two recrystallizations from ethanol provided 1.88 grams (50%) of tan crystals, mp 130-133 C. The 1H and 13C NMR spectra of the final product and all intermediates were consistent with the structures of the target compounds.

Reference： [1]Patent: US2008/114177,2008,A1 .Location in patent: Page/Page column 4

80
[ 23814-12-2 ]
[ 181042-39-7 ]
[ 892865-70-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 80℃; for 2h;	Example 5; Synthesis of 1H-Benzotriazole-5-carboxylic acid 7,7,8,8,9,9,10,10,10-nonafluoro-decyl ester; Benzotriazole-5-carboxylic acid (3.75 grams, 23.0 mmol) was dissolved in 15 milliliters of anhydrous DMF and stirred under N2. N,N'-carbonyldiimidazole (3.75 grams, 23.0 mmol) was added to the reaction and the mixture was stirred until gas evolution ceased (about 5 minutes). 7,7,8,8,9,9,10,10,10-nonafluorodecanol (5.45 milliliters, 23.0 mmol) was added and the mixture was heated to 80 C. for 2 days. The reaction mixture was cooled and concentrated under reduced pressure to give a dark brown syrup. The syrup was poured into 150 milliliters of ice water followed by rapid stirring. After 15 minutes, the mixture was filtered to give a pasty, brown sludge that was rinsed with H2O and dried somewhat with suction. The brown sludge was then transferred to a flask and dissolved in ethyl acetate. The solvent was evaporated to give an oil that started to solidify upon standing. The material was dissolved in about 10 milliliters of ethyl acetate and applied to a 6×3 cm pad of SiO2. The pad was eluted with about 200 milliliters of ethyl acetate and the filtrate was concentrated give 11 grams of brown solid. The brown solid was dissolved in 100 milliliters of hot ethanol and treated with 5 grams of charcoal. The hot solution was filtered through a pad of Celite and concentrated to give a light brown solid. Crystallization from 25 milliliters of 10% ethyl acetate/hexanes gave 3.6 grams of the desired product and an off-white powder, m.p. 86.5-90.5 C. 1H NMR confirmed the predicted structure. Anal. Calcd for C17H16F9N3O2: C, 43.88; H, 3.47; N, 9.03. Found: C, 43.87, H, 3.44, N, 8.93.

Reference： [1]Patent: US2008/114177,2008,A1 .Location in patent: Page/Page column 6

81
[ 23814-12-2 ]
[ 3792-02-7 ]
[ 1025027-08-0 ]

Yield	Reaction Conditions	Operation in experiment
52%	With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; at 70℃; for 48h;	To a mixture of 8.76 grams (30 mmol) of 5,5,6,6,7,7,8,8,8-nonafluoro-1-octanol and 9.79 grams (60 mmol) of benzotriazole-5-carboxylic acid in 200 milliliters of a 9:1 mixture of tetrahydrofuran and dimethyl formamide were added 12.38 grams (60 mmol) of N,N-dicyclohexylcarbodiimide and 0.73 grams (6 mmol) of 4-(dimethylamino)pyridine, and the resultant mixture was heated at 70 C. for 48 hours. The mixture was filtered, and the filtrate was concentrated to a tan solid. The crude product was slurried in 250 milliliters of ethyl acetate, the mixture was filtered, and the filtrate was concentrated to a tan solid. Flash chromatography on silica with ethyl acetate followed by recrystallization from a 95:5 mixture of heptane and 2-propanol afforded 6.77 grams (52%) of tan crystals, mp 98-101 C. The 1H and 13C NMR spectra of the final product and all intermediates were consistent with the structures of the target compounds.

Reference： [1]Patent: US2008/114177,2008,A1 .Location in patent: Page/Page column 5

82
[ 23814-12-2 ]
[ 36096-97-6 ]
[ 1025027-05-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; at 70℃; for 48h;	To a mixture of 9.41 grams (24 mmol) of 12,12,13,13,14,14,15,15,15-nonafluoro-1-pentadecanol and 8.16 grams (50 mmol) of benzotriazole-5-carboxylic acid in 200 milliliters of a 9:1 mixture of tetrahydrofuran and dimethyl formamide were added 10.32 grams (50 mmol) of N,N-dicyclohexylcarbodiimide and 0.61 grams (5 mmol) of 4-(dimethylamino)pyridine, and the resultant mixture was heated at 70 C. for 48 hours. The mixture was filtered, and the filtrate was concentrated to a dark semisolid. The crude product was slurried in 200 milliliters of ethyl acetate, the mixture was filtered, and the filtrate was concentrated to a tan solid. Two recrystallizations from a 9:1 mixture of methanol and water afforded 9.26 grams (74%) of tan crystals, mp 99-102 C. The 1H and 13C NMR spectra of the final product and all intermediates were consistent with the structures of the target compounds.

Reference： [1]Patent: US2008/114177,2008,A1 .Location in patent: Page/Page column 4

83
[ 23814-12-2 ]
[ 627909-31-3 ]
[ 1025027-07-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; at 70℃; for 48h;	To a mixture of 0.50 grams (0.9 mmol) of 23,23,24,24,25,25,26,26,26-nonafluoro-1-hexacosanol and 0.49 grams (3.0 mmol) of benzotriazole-5-carboxylic acid in 10 milliliters of a 9:1 mixture of tetrahydrofuran and dimethyl formamide were added 0.62 grams (3.0 mmol) of N,N-dicyclohexylcarbodiimide and 0.04 grams (0.3 mmol) of 4-(dimethylamino)pyridine, and the resultant mixture was heated at 70 C. for 48 hours. The mixture was filtered, and the filtrate was concentrated to a dark tan semisolid. The crude product was slurried in 30 milliliters of tetrahydrofuran, the mixture was filtered, and the filtrate was concentrated to a tan solid. Recrystallization from methanol provided 0.50 grams (79%) of tan crystals, mp 106-108 C. The 1H and 13C NMR spectra of the final product and all intermediates were consistent with the structures of the target compounds.

Reference： [1]Patent: US2008/114177,2008,A1 .Location in patent: Page/Page column 5

84
[ 23814-12-2 ]
[ 73605-91-1 ]

Yield	Reaction Conditions	Operation in experiment
	conc. sulphuric acid; In ethanol; ethyl acetate;	1H-Benzotriazole-5-carboxylic acid ethyl ester [24] A suspension of <strong>[23814-12-2]1H-benzotriazole-5-carboxylic acid</strong> in ethanol (50ml, excess) was gently refluxed overnight in the presence of conc. sulphuric acid (0.5ml), by which time TLC (A) indicated complete reaction. Ethanol was removed in vacuo to afford an aqueous residue that was dissolved in ethyl acetate (30ml) and extracted with sodium chloride solution (4x20ml). The organic layer was dried over sodium sulphate and removal of solvent in vacuo afforded the pure ester [24] in 86% yield. Rf(A) 0.75; deltaH(400MHz; DMSO-d6) 1.36 (3H, t, CH3) 4.36 (2H, q, CH2) 7.94 (2H, br s, BT) 8.59 (1H, br s, BT) 16.03 (1H, s, NH); m/z (EI-HR) 191.07023 [(M) calc. for C9H9N3O2 191.06948].

Reference： [1]Patent: EP1272827,2008,B1
[2]Chinese Chemical Letters,2017,vol. 28,p. 919 - 926

85
[ 23814-12-2 ]
[ 74115-12-1 ]
[ 1026251-18-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 5761 - 5777

86
(S)-(+)-1-isopropyl-1-methyl-prop-2-ynylamine hydrochloride [ No CAS ]
[ 23814-12-2 ]
[7-((S)-2-azido-hexanolylamino)-4-methyl-2-oxo-2H-chromen-3-yl]acetyl-Wang resin [ No CAS ]
[ 1029431-03-5 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 6404 - 6410

87
[ 23814-12-2 ]
C₂₅H₃₂N₅O₅Pol [ No CAS ]
C₃₂H₃₅N₈O₆Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-trimethyl-pyridine; HATU; In N,N-dimethyl-formamide; at 20℃; for 48h;	Amide substrate 21[0116] To resin 15 (0.115 g, 0.0750 mmol), preswollen in THF, was added a 0.02 M solution of the HCl salt of propargylamine 16 (0.025 g, 0.17 mmol) and /-Pr2EtN (1.3 mL, 7.5 <n="44"/>mmol) in THF (8.2 mL). CuI (0.043 g, 0.23 mmol) was then added and the mixture was shaken for 48 h. After removal of the solution, the resin was washed with three portions (20 mL) each of THF, CH3OH, CH3CN, and THF to afford support-bound amine intermediate 17. Resin 17 was swollen with three portions (20 mL) of DMF. A 0.4 M solution of HATU (0.200, 0.530 mmol), 2,4,6-collidine (0.070 mL, 0.53 mmol), and benzotriazole-5-carboxylic acid (0.086 g, 0.53 mmol) in DMF (1.3 mL) was added to the resin, and the mixture was shaken for 48 h. After removal of the solution, the resin was washed with three portions (20 mL) each of DMF, THF, CH3OH, THF, and CH2Cl2, and then the product was cleaved from support and purified following Procedure C to afford 7.9 mg (17%) of 21 as a white powder. 1H NMR (500 MHz, DMSO-d6): delta 0.74 (d, 3H, J = 6.5), 0.83 (t, 3H, J = 7.2), 0.93 (d, 3H, J = 6.5), 1.05-1.38 (m, 4H), 1.76 (s, 3H), 2.14-2.22 (m, 2H), 2.36 (s, 3H), 2.68 (sept, IH, J = 6.5), 3.58 (s, 2H), 5.45 (dd, IH, J= 7.5, 8.0), 7.49 (d, IH, J= 8.5), 7.72 (s, IH), 7.79-7.82 (m, 2H), 7.90 (br s, IH), 8.16 (s, IH), 8.25 (s, IH), 8.40 (br s, IH), 10.96 (s, IH), 12.38 (br s, IH). HRMS-FAB (m/z): [MNa]+ calcd for C32H36N8O6Na, 651.2656; found, 651.2660.

Reference： [1]Patent: WO2009/75778,2009,A2 .Location in patent: Page/Page column 42-43

88
[ 23814-12-2 ]
C₅₅H₆₀F₂N₇O₁₄P [ No CAS ]
C₆₂H₆₃F₂N₁₀O₁₅P [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 13072 - 13079

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[ CAS No. 23814-12-2 ] {[proInfo.proName]}

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[ 23814-12-2 ] Synthesis Path-Downstream 1~88

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