24372-46-1|5-(Dimethylamino)thiophene-2-carbaldehyde| Ambeed

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Quality Control of [ 24372-46-1 ] Purity: 98% SDS Specification

COA

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NMR

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Product Details of [ 24372-46-1 ]

CAS No. :	24372-46-1
Formula :	C₇H₉NOS
M.W :	155.22
SMILES Code :	O=CC1=CC=C(N(C)C)S1
MDL No. :	MFCD00708772
InChI Key :	RRQFJMCAGDOEPI-UHFFFAOYSA-N
Pubchem ID :	3157939

Safety of [ 24372-46-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 24372-46-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	5
Fraction Csp3	0.29
Num. rotatable bonds	2
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	43.91
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	48.55 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.79
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.85
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.63
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.44
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.18
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.58

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.21
Solubility	0.966 mg/ml ; 0.00623 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.49
Solubility	0.502 mg/ml ; 0.00323 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.71
Solubility	3.02 mg/ml ; 0.0195 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.93 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.14

Application In Synthesis of [ 24372-46-1 ]

* 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 [ 24372-46-1 ]

[ 24372-46-1 ] Synthesis Path-Downstream 1~35

1
[ 7648-01-3 ]
[ 24372-46-1 ]
5-(5-dimethylamino-thiophen-3-ylmethylene)-3-ethyl-2-thioxo-thiazolidin-4-one [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1975,vol. 11,p. 273 - 277.
Khimiya Geterotsiklicheskikh Soedinenii,1975,vol. 11,p. 316 - 320.

2
[ 5217-47-0 ]
[ 24372-46-1 ]
[ 55952-96-0 ]

References: [1]Chemistry of Heterocyclic Compounds,1975,vol. 11,p. 273 - 277.
Khimiya Geterotsiklicheskikh Soedinenii,1975,vol. 11,p. 316 - 320.

3
[ 121-69-7 ]
[ 24372-46-1 ]
C₁₅H₁₉N₂S⁽¹⁺⁾*ClO₄^(1-) [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1975,vol. 11,p. 273 - 277.
Khimiya Geterotsiklicheskikh Soedinenii,1975,vol. 11,p. 316 - 320.

4
[ 606-55-3 ]
[ 24372-46-1 ]
[ 55952-79-9 ]

References: [1]Chemistry of Heterocyclic Compounds,1975,vol. 11,p. 273 - 277.
Khimiya Geterotsiklicheskikh Soedinenii,1975,vol. 11,p. 316 - 320.

5
[ 14933-76-7 ]
[ 24372-46-1 ]
[ 36986-83-1 ]

References: [1]Soviet progress in chemistry,1972,vol. 38,p. 69 - 72.
Ukrainskii Khimicheskii Zhurnal (Russian Edition),1972,vol. 38,p. 68 - 70.

6
[ 64873-75-2 ]
[ 24372-46-1 ]
2,2'-bis-[2-(5-dimethylamino-thiophen-2-yl)-vinyl]-3,3'-ethane-1,2-diyl-bis-benzothiazolium; diperchlorate [ No CAS ]

References: [1]Soviet progress in chemistry,1977,vol. 43,p. 57 - 61.
Ukrainskii Khimicheskii Zhurnal (Russian Edition),1977,vol. 43,p. 953 - 956.

7
[ 19760-15-7 ]
[ 24372-46-1 ]
[ 55953-27-0 ]

References: [1]Chemistry of Heterocyclic Compounds,1975,vol. 11,p. 273 - 277.
Khimiya Geterotsiklicheskikh Soedinenii,1975,vol. 11,p. 316 - 320.

8
[ 38870-30-3 ]
[ 24372-46-1 ]
2,7-bis-[trans-2-(5-dimethylamino-thiophen-2-yl)-vinyl]-3,8-dimethyl-benzo[1,2-d;3,4-d']bisthiazolediium; diperchlorate [ No CAS ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1972,vol. 8,p. 2014 - 2018.
Zhurnal Organicheskoi Khimii,1972,vol. 8,p. 1968 - 1973.

9
[ 38133-78-7 ]
[ 24372-46-1 ]
2,7-bis-[trans-2-(5-dimethylamino-thiophen-2-yl)-vinyl]-3,6-diethyl-benzo[1,2-d;4,3-d']bisthiazolediium; diperchlorate [ No CAS ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1972,vol. 8,p. 2014 - 2018.
Zhurnal Organicheskoi Khimii,1972,vol. 8,p. 1968 - 1973.

10
[ 24372-46-1 ]
1-ethyl-2,3,3-trimethyl-3H-indolium perchlorate [ No CAS ]
2-[2-(5-dimethylamino-thiophen-2-yl)-vinyl]-1-ethyl-3,3-dimethyl-3H-indolium; perchlorate [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1975,vol. 11,p. 273 - 277.
Khimiya Geterotsiklicheskikh Soedinenii,1975,vol. 11,p. 316 - 320.

11
[ 24372-46-1 ]
[ 40671-20-3 ]
[ 38133-77-6 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1972,vol. 8,p. 2014 - 2018.
Zhurnal Organicheskoi Khimii,1972,vol. 8,p. 1968 - 1973.

12
[ 24372-46-1 ]
[ 89-25-8 ]
[ 55952-97-1 ]

References: [1]Chemistry of Heterocyclic Compounds,1975,vol. 11,p. 273 - 277.
Khimiya Geterotsiklicheskikh Soedinenii,1975,vol. 11,p. 316 - 320.

13
[ 24372-46-1 ]
[ 89-25-8 ]
[ 55952-90-4 ]

References: [1]Chemistry of Heterocyclic Compounds,1975,vol. 11,p. 273 - 277.
Khimiya Geterotsiklicheskikh Soedinenii,1975,vol. 11,p. 316 - 320.

14
[ 3216-50-0 ]
[ 68-12-2 ]
[ 24372-46-1 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1969,vol. 311,p. 827 - 843.

15
[ 81903-37-9 ]
[ 24372-46-1 ]
[ 81903-33-5 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1982,p. 183 - 189.
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 206 - 213.

16
[ 24372-46-1 ]
1,5,6,9-tetrahydro-1,1,2,8,9,9-hexamethyl-4H-dipyrrolo<1,2,3-e,f:3,2,1-n,o>naphtho<2,3-b><1,4>diazepinium diperchlorate [ No CAS ]
2,8-bis<2-(5-dimethylamino-2-thienyl)vinyl>-1,5,6,9-tetrahydro-1,1,9,9-tetramethyl-4H-dipyrrolo<1,2,3-e,f:3,2,1-n,o>naphtho<2,3-b><1,4>diazepinium diiodide [ No CAS ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1982,p. 183 - 189.
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 206 - 213.

17
[ 4701-17-1 ]
[ 124-40-3 ]
[ 24372-46-1 ]

Yield	Reaction Conditions	Operation in experiment
82.5%	In water; at 100℃; for 12.0h;	Synthesis of 5-dimethylamino-2-thiophenecarboxyaldehyde (30) 5-Bromo-2-thiophenecarboxyaldehyde (1 g, 5.23 mmol) and dimethylamine (1.64 mL, 15.69 mmol) were mixed, followed by addition of purified water (3 mL). The mixture was reacted at 100C for 12 h, and then the layers were separated with chloroform (50 mL x 2) and purified water (50 mL), the chloroform layer was dried with anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/1) as an elution solvent to obtain Compound 30. Yield 670 mg (yield rate 82.5%). 1H NMR (300 MHz, CDCl3) delta 3.10 (s, 6H), 5.96 (s, 1H), 7.45 (s, 1H), 9.44 (s, 1H).
Ca. 60%	With toluene-4-sulfonic acid; In water; at 100℃; for 24.0h;	To a 100 mL round bottom flask was added 5-bromothiophene-2-carbaldehyde (6 g, 32 mmol)And dimethylamine aqueous solution (16.2 mL, content 40%, 128 mmol)To a solution of p-toluenesulfonic acid (0.55 g, 3.2 mmol) as a catalyst,The reaction was refluxed at 100 C for about 24 h,Dimethylamine is volatile,Add about 8 mL of dimethylamine aqueous solution every 6 hours,Process point board tracking,Until 5-bromothiophene-2-carbaldehyde is completely reacted;After completion of the reaction, the mixture was cooled to room temperature,Down to about 60 mL of deionized water,Stirred at room temperature for 0.5 h,Extracted with 3 x 40 mL of dichloromethane;After extraction, the organic phase was combined,Dried over anhydrous sodium sulfate,Filter,Steaming concentrated solution;Using silica gel column chromatography separation and purification (eluent:Ethyl acetate / petroleum ether = 1/1),Finally, a dark red target product (yield of about 60%) was obtained.
Ca. 60%	With toluene-4-sulfonic acid; In water; at 100℃; for 24.0h;	6 g of 5-bromothiophene-2-carbaldehyde and 16.2 mL of a 40% aqueous solution of dimethylamine were added to a round bottom flask equipped with a condensing device. 0.5 g of p-toluenesulfonic acid was added as a catalyst. The reaction was carried out by heating to 100 C. During the process, the raw material was monitored for 5-bromothiophene-2-ylformaldehyde. The dimethylamine was volatile, and a certain amount of dimethylamine aqueous solution was added every 6 hours until the reaction of 5-bromothiophene-2 formaldehyde was complete, and the reaction took about 24 hours; After completion, it was cooled to room temperature, 60 mL of deionized water was added, stirred for 0.5 h, and then extracted with dichloromethane; the organic phase was combined, dried over anhydrous sodium sulfate for 24 h, then filtered, and concentrated by rotary evaporation; The method was separated and purified (eluent ethyl acetate: petroleum ether = 1:1, Rf = 0.2) to give red 5-(dimethylamino)thiophene-2-carbaldehyde in a yield of about 60%.

References: [1]Synlett,1998,p. 383 - 384.
[2]Patent: EP2030635,2009,A1 .Location in patent: Page/Page column 26; 50.
[3]Chemical Communications,2015,vol. 51,p. 17124 - 17127.
[4]Patent: CN107090190,2017,A .Location in patent: Paragraph 0046; 0047; 0048; 0049.
[5]Patent: CN104945307,2017,B .Location in patent: Paragraph 0083; 0088-0089.
[6]Journal of the American Chemical Society,2001,vol. 123,p. 2810 - 2824.

19
[ 27074-03-9 ]
[ 24372-46-1 ]
5-[1-(5-Dimethylamino-thiophen-2-yl)-meth-(Z)-ylidene]-1,4-dimethyl-2,6-dioxo-1,2,5,6-tetrahydro-pyridine-3-carbonitrile [ No CAS ]

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 2810 - 2824.

20
[ 24372-46-1 ]
1-butyl-4-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyridine-3-carbonitrile [ No CAS ]
1-Butyl-5-[1-(5-dimethylamino-thiophen-2-yl)-meth-(Z)-ylidene]-4-methyl-2,6-dioxo-1,2,5,6-tetrahydro-pyridine-3-carbonitrile [ No CAS ]

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 2810 - 2824.

21
[ 3199-50-6 ]
[ 24372-46-1 ]
1-(5-bromo-2-furyl)-3-(5-dimethylamino-2-thienyl)-prop-2-en-1-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 6388 - 6396.

22
[ 30955-94-3 ]
[ 24372-46-1 ]
3-(5-dimethylamino-2-thienyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 6388 - 6396.

23
[ 13329-40-3 ]
[ 24372-46-1 ]
3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 6388 - 6396.

24
[ 24372-46-1 ]
[ 650628-65-2 ]
5-(dimethylamino)thiophene-2-carbaldehyde [1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyrrolidine; In ethanol; for 12.0h;Heating / reflux;	A mixture of [4-HYDRAZINO-1- (3-METHOXYPHENYL)-1 H-PYRAZOLO] [3, [4-DJPYRIMIDINE] (Intermediates Example T) (100 mg, 0.392 [MMOL),] [5- (DIMETHYLAMINO)-2-] [THIOPHENECARBALDEHYDE] (77 mg, [0.] 499 [MMOL),] and [PYRROLIDINE] (2 drops) in [ETOH] (10 mL) was heated at reflux for 12 h. The solid was filtered and washed with hexanes to yield product (142 mg, 95%) as a yellow solid. 'H NMR (400 MHz, DMSO) [8] 11.97 (s, 1 H), 8.48 (s, 1 H), 8.38 (s, [1] H), 8.22 (s, [1] H), 7.87- 7.83 (m, 2H), 7.44 (t, 1 H), 7.16 (d, [1] H), 6.91 (m, 1 H), 5.90 (d, 1 H), 3.82 (s, 3H), 3.00 (s, 6H) ppm; ES-MS m/z 394 [(MH+).]

References: [1]Patent: WO2004/9602,2004,A1 .Location in patent: Page 227.

25
[ 865876-82-0 ]
[ 24372-46-1 ]
3-{(2E)-3-[4-(dimethylamino)-2-thienyl]prop-2-enoyl}-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 8988 - 8998.
[2]Russian Journal of Organic Chemistry,2008,vol. 44,p. 1054 - 1060.

26
[ 3199-50-6 ]
[ 24372-46-1 ]
1-(5-bromo-2-furyl)-3-(5-dimethylamino-2-thienyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11.4%	With potassium hydroxide; In ethanol; water; at 20℃; for 3h;	Synthesis of 1-(5-bromo-2-furyl)-3-(5-dimethylamino-2-thienyl)-prop-2-en-1-one (35) Compound 29 (97 mg, 0.51 mmol) and Compound 30 (75 mg, 0.48 mmol) were dissolved in ethanol (1.5 mL), and 10% aqueous potassium hydroxide (0.5 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 3 h, then the solvent was evaporated under reduced pressure, followed by addition of 1 N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The mixture was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (2/7) as an elution solvent to obtain Compound 35. Yield 18 mg (yield rate 11.4%). 1H NMR (300 MHz, CDCl3) delta 3.08 (s, 6H), 5.85 (d, J = 3.9 Hz, 1H), 6.48 (d, J = 3.6 Hz, 1H), 6.72 (d, J = 15 Hz, 1H), 7.14-7.16 (m, 2H), 7.91 (d, J = 15 Hz, 1H). MS m/z 327 (MH+).

References: [1]Patent: EP2030635,2009,A1 .Location in patent: Page/Page column 27; 50.

27
[ 30955-94-3 ]
[ 24372-46-1 ]
3-(5-dimethylamino-2-thienyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.9%	With potassium hydroxide; In ethanol; water; at 20℃; for 3.0h;	Synthesis of 3-(5-dimethylamino-2-thienyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one (37) 2-Acetyl-5-iodothiophene (123 mg, 0.49 mmol) and Compound 30 (76 mg, 0.49 mmol) were dissolved in ethanol (3 mL), and 10% aqueous potassium hydroxide (1 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 3 h, then the solvent was evaporated under reduced pressure, followed by addition of 1 N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The mixture was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (1/4) as an elution solvent to obtain compound 37. Yield 15 mg (yield rate 7.9%). 1H NMR (300 MHz, CDCl3) delta 3.07 (s, 6H), 5.85 (d, J = 4.2 Hz, 1H), 6.63 (d, J = 14.7 Hz, 1H), 7.15 (d, J = 4.5 Hz, 1H), 7.29 (d, J = 3.9 Hz, 1H), 7.38 (d, J = 4.2 Hz, 1H), 7.87 (d, J = 14.7 Hz, 1H). MS m/z 389 (M+).

References: [1]Patent: EP2030635,2009,A1 .Location in patent: Page/Page column 27; 50.

28
[ 13329-40-3 ]
[ 24372-46-1 ]
3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.7%	With potassium hydroxide; In ethanol; water; at 20℃; for 3.0h;	Synthesis of 3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one (33) 4-Iodoacetophenone (246 mg, 1.00 mmol) and Compound 30 (155 mg, 1.00 mmol) were dissolved in ethanol (5 mL), followed by addition of 10% aqueous potassium hydroxide (7.5 mL). The mixture was reacted at room temperature for 3 h, the layers were separated with ethyl acetate (50 mL x 2), and the ethyl acetate layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/4) as an elution solvent to obtain Compound 33. Yield 18 mg (yield rate 4.7%). 1H NMR (300 MHz, CDCl3) delta 3.04 (s, 6H), 5.22 (d, J = 3.9 Hz, 1H), 6.80 (d, J = 3.6 Hz, 1H), 6.89 (d, J = 15.0 Hz, 1H), 7.46 (d, J = 14.7 Hz, 1H), 7.70 (d, J = 8.1 Hz, 2H), 7.81 (d, J = 8.7 Hz, 2H). MS m/z 383 (M+).

References: [1]Patent: EP2030635,2009,A1 .Location in patent: Page/Page column 26-27; 50.

29
2,2-difluoro-4-methyl-5,6-[2H-benzopyrano(3,4-e)-2-one]-1,3,2-dioxaborine [ No CAS ]
[ 24372-46-1 ]
4-difluoroboryloxy-3-[(E)-3-[5-(N,N-dimethylamino)-2-thienyl]prop-2-enoyl]coumarin [ No CAS ]

References: [1]Russian Chemical Bulletin,2008,vol. 57,p. 1508 - 1515.
[2]Russian Chemical Bulletin,2008,vol. 57,p. 1508 - 1515.

30
[ 4701-17-1 ]
[ 24372-46-1 ]

Yield	Reaction Conditions	Operation in experiment
82.5%	With dimethyl amine; In hexane; water; ethyl acetate;	Synthesis of 5-dimethylamino-2-thiophenecarboxyaldehyde (30) 5-Bromo-2-thiophenecarboxyaldehyde (1 g, 5.23 mmol) and dimethylamine (1.64 mL, 15.69 mmol) were mixed, followed by addition of purified water (3 mL). The mixture was reacted at 100 C. for 12 h, and then the layers were separated with chloroform (50 mL*2) and purified water (50 mL), the chloroform layer was dried with anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/1) as an elution solvent to obtain Compound 30. Yield 670 mg (yield rate 82.5%). 1H NMR (300 MHz, CDCl3) delta 3.10 (s, 6H), 5.96 (s, 1H), 7.45 (s, 1H), 9.44 (s, 1H).

References: [1]Patent: US2010/278733,2010,A1 .

31
[ 3199-50-6 ]
aqueous potassium hydroxide [ No CAS ]
[ 24372-46-1 ]
1-(5-bromo-2-furyl)-3-(5-dimethylamino-2-thienyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11.4%	With sodium hydroxide; In ethanol; hexane; ethyl acetate;	Synthesis of 1-(5-bromo-2-furyl)-3-(5-dimethylamino-2-thienyl)-prop-2-en-1-one (35) Compound 29 (97 mg, 0.51 mmol) and Compound 30 (75 mg, 0.48 mmol) were dissolved in ethanol (1.5 mL), and 10% aqueous potassium hydroxide (0.5 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 3 h, then the solvent was evaporated under reduced pressure, followed by addition of 1 N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The mixture was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (2/7) as an elution solvent to obtain Compound 35. Yield 18 mg (yield rate 11.4%). 1H NMR (300 MHz, CDCl3) delta 3.08 (s, 6H), 5.85 (d, J=3.9 Hz, 1H), 6.48 (d, J=3.6 Hz, 1H), 6.72 (d, J=15 Hz, 1H), 7.14-7.16 (m, 2H), 7.91 (d, J=15 Hz, 1H). MS m/z 327 (MH+).

References: [1]Patent: US2010/278733,2010,A1 .

32
[ 30955-94-3 ]
aqueous potassium hydroxide [ No CAS ]
[ 24372-46-1 ]
3-(S-dimethylamino-2-thienyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.9%	With sodium hydroxide; In ethanol; hexane; ethyl acetate;	Synthesis of 3-(S-dimethylamino-2-thienyl)-1-(5-iodo-2-thienyl)-prop-2-en-1-one (37) 2-Acetyl-5-iodothiophene (123 mg, 0.49 mmol) and Compound 30 (76 mg, 0.49 mmol) were dissolved in ethanol (3 mL), and 10% aqueous potassium hydroxide (1 mL) was added dropwise with stirring. The mixture was stirred at room temperature for 3 h, then the solvent was evaporated under reduced pressure, followed by addition of 1 N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The mixture was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (1/4) as an elution solvent to obtain compound 37. Yield 15 mg (yield rate 7.9%). 1H NMR (300 MHz, CDCl3) delta 3.07 (s, 6H), 5.85 (d, J=4.2 Hz, 1H), 6.63 (d, J=14.7 Hz, 1H), 7.15 (d, J=4.5 Hz, 1H), 7.29 (d, J=3.9 Hz, 1H), 7.38 (d, J=4.2 Hz, 1H), 7.87 (d, J=14.7 Hz, 1H). MS m/z 389 (M+).

References: [1]Patent: US2010/278733,2010,A1 .

33
aqueous potassium hydroxide [ No CAS ]
[ 13329-40-3 ]
[ 24372-46-1 ]
3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.7%	In ethanol; hexane; ethyl acetate;	Synthesis of 3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one (33) 4-Iodoacetophenone (246 mg, 1.00 mmol) and Compound 30 (155 mg, 1.00 mmol) were dissolved in ethanol (5 mL), followed by addition of 10% aqueous potassium hydroxide (7.5 mL). The mixture was reacted at room temperature for 3 h, the layers were separated with ethyl acetate (50 mL*2), and the ethyl acetate layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/4) as an elution solvent to obtain Compound 33. Yield 18 mg (yield rate 4.7%). 1H NMR (300 MHz, CDCl3) delta 3.04 (s, 6H), 5.22 (d, J=3.9 Hz, 1H), 6.80 (d, J=3.6 Hz, 1H), 6.89 (d, J=15.0 Hz, 1H), 7.46 (d, J=14.7 Hz, 1H), 7.70 (d, J=8.1 Hz, 2H), 7.81 (d, J=8.7 Hz, 2H). MS m/z 383 (M+).

References: [1]Patent: US2010/278733,2010,A1 .

34
[ 1217552-67-4 ]
[ 24372-46-1 ]
4-difluoroboryloxy-3-[3-(5-dimethylamino-2-thienyl)prop-2-E-enoyl]-1-methyl-2-quinolone [ No CAS ]

References: [1]Russian Chemical Bulletin,2008,vol. 57,p. 1734 - 1739.
[2]Russian Chemical Bulletin,2008,vol. 57,p. 1734 - 1739.

35
[ 1217552-67-4 ]
[ 24372-46-1 ]
[ 1217552-81-2 ]

References: [1]Russian Chemical Bulletin,2008,vol. 57,p. 1734 - 1739.

Historical Records

Technical Information

• Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Vilsmeier Reagent • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 24372-46-1 ]

Aldehydes

A157386 [207290-72-0]

5-(4-Hydroxypiperidin-1-yl)thiophene-2-carbaldehyde

Similarity: 0.75

A108216 [4521-33-9]

5-Nitrothiophene-2-carboxaldehyde

Similarity: 0.68

A161612 [98-03-3]

Thiophene-2-carbaldehyde

Similarity: 0.62

A270093 [13679-70-4]

5-Methylthiophene-2-carbaldehyde

Similarity: 0.61

A101751 [21512-16-3]

5-Formylthiophene-2-carbonitrile

Similarity: 0.55

Amines

A247743 [14597-58-1]

Methyl 5-aminothiophene-2-carboxylate

Similarity: 0.66

A127214 [52532-63-5]

5-Aminothiophene-2-carbonitrile

Similarity: 0.61

A586086 [51486-03-4]

2-Amino-5-methylthiophene-3-carboxamide

Similarity: 0.54

A143797 [4521-30-6]

Benzo[b]thiophen-2-amine

Similarity: 0.54

A289215 [138564-58-6]

2-Amino-5-methylthiophene-3-carbonitrile

Similarity: 0.54

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CAS No.: 24372-46-1

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