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Quality Control of [ 53174-98-4 ] Purity: 97% SDS Specification

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Product Details of [ 53174-98-4 ]

CAS No. :	53174-98-4
Formula :	C₈H₅NOS
M.W :	163.20
SMILES Code :	O=CC1=CC2=CC=CN=C2S1
MDL No. :	MFCD07772791
InChI Key :	HGZQKYOLRLVMHZ-UHFFFAOYSA-N
Pubchem ID :	289925

Safety of [ 53174-98-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 53174-98-4 ]

* 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 [ 53174-98-4 ]

[ 53174-98-4 ] Synthesis Path-Downstream 1~27

1
[ 272-23-1 ]
[ 68-12-2 ]
[ 53174-98-4 ]

Yield	Reaction Conditions	Operation in experiment
66%		Thieno[2,3-b]pyridine-2-carbaldehyde: In an atmosphere of argon a mixture of 1.3 mL (2.08 mmol) of 0.8 M n-butyllithium in hexane and 0.3 mL (3.3 mmol) of N,N,N?,N?-tetramethylethylenediamine was stirred magnetically at room temperature for 30 minutes, diluted with 5 mL of hexane, cooled in a bath of dry ice-ethanol, and treated (with vigorous stirring) dropwise (from a syringe with a small needle) with 0.23 g (1.7 mmol) of thieno[2,3-b] pyridine. The mixture was stirred in the bath for 7 h longer and then for 12 h while it warmed to room temperature. It was cooled in ice, treated with 0.15 g (2.1 mmol) of dimethylformamide, stirred for one hour, and then treated successively with 1 mL of ethanol, 3 mL of saturated aqueous ammonium chloride solution, and 4 mL of water. The layers were separated. The organic layer (plus chloroform extracts of the aqueous layer) was dried (magnesium sulfate) and evaporated. The residue was triturated with hexane to give 0.18 g (66%) of brown solid; m.p. 131.5-132.5 C. Recrystallizations from ethanol (once with charcoal) gave white needles. 1H NMR (300 MHz, CDCl3) ppm 7.41 (dd, J = 4.5 Hz, 8.1 Hz, 1 H), 7.99 (s, 1 H), 8.24 (dd, J = 1.8 Hz, 8.1 Hz, 1 H), 8.73 (dd, J = 1.8 Hz, 4.5 Hz, 1 H), 10.12 (s, 1 H). 13C NMR (75 MHz, CDCl3) ppm 120.7, 131.8, 132.3, 134.0, 143.2, 150.5, 163.8, 185.0. IR (CHCl3, cm-1) 1682 (C=O). MS (EI, 70 eV): m/z [%] = 162[M]+ (100), 134[M-CO]+ (26). HRMS (FAB+) calculated for C8H6NOS [M+1] 164.0170, found 164.0167.

References: [1]Tetrahedron Letters,2017,vol. 58,p. 1952 - 1956.
[2]Tetrahedron Letters,1994,vol. 35,p. 1011 - 1014.
[3]Journal of Heterocyclic Chemistry,1974,vol. 11,p. 355 - 361.

2
[ 75-52-5 ]
[ 53174-98-4 ]
[ 53175-07-8 ]

References: [1]Journal of Heterocyclic Chemistry,1974,vol. 11,p. 355 - 361.

3
[ 7306-64-1 ]
[ 53174-98-4 ]
[ 156736-78-6 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1011 - 1014.

4
[ 35023-80-4 ]
[ 53174-98-4 ]
[ 156736-72-0 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1011 - 1014.

5
[ 53174-98-4 ]
[ 131337-81-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium borohydrid; In ethanol;	EXAMPLE N 2-Chloromethyl-thieno[2,3-b]pyridine Thieno[2,3-b]pyridine-2-carboxaldehyde (1.63 g) prepared according to J. Het. Chem. 355 (1974) was dissolved in ethanol (20 ml) and to the solution was added sodium borohydride (0.19 g). After 30 minutes the solution was evaporated to dryness and the residue extracted with methylene chloride (50 ml). The organic extract was washed with water (2*25 ml), the extract dried and then evaporated to obtain 2-hydroxymethylthieno[2,3-b]pyridine (1.40 g) as an amber oil. 'H-NMR (CDCl3,60 MHz): 4.9 (s, 1H), 6.3 (s, 1H), 6.9 s, 1H), 7.1 (m, 1H), 7.8 (m, 1H), 8.4 (m, 1H).

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7577 - 7589.
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 457 - 465.
[3]Patent: US4939140,1990,A .

6
[ 53174-98-4 ]
[ 14131-84-1 ]
C₂₀H₂₄N₂O₆S [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1011 - 1014.

7
[ 53174-98-4 ]
C₂₈H₂₆NO₂PS [ No CAS ]
6-carboethoxy-2-methyl-4-(2'-thieno<2,3-b>pyridine)thieno<3,2-c>pyridine [ No CAS ]

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,1999,vol. 55,p. 1035 - 1048.

8
[ 53174-98-4 ]
[ 150323-38-9 ]
N-(2(R)-hydroxy-1(S)-indanyl)-2(R)-phenylmethyl-4(S)-hydroxy-5-(1-(4-(2-thieno[2,3-b]pyridylmethyl)-2(S)-N'-(tert-butylcarboxamido)piperazinyl))pentanamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3386 - 3399.

9
[ 53174-98-4 ]
N-((R)-1-Thieno[2,3-b]pyridin-2-yl-ethyl)-hydroxylamine [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1011 - 1014.

10
[ 53174-98-4 ]
C₁₀H₁₁N₃O₂S [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1011 - 1014.

11
[ 53174-98-4 ]
N-[(3aR,4R,6S,6aR)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-N-((R)-1-thieno[2,3-b]pyridin-2-yl-ethyl)-hydroxylamine [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1011 - 1014.

12
[ 53174-98-4 ]
N-[(3aR,4R,6S,6aR)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-N-((S)-1-thieno[2,3-b]pyridin-2-yl-ethyl)-hydroxylamine [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1011 - 1014.

13
[ 53174-98-4 ]
[ 156736-77-5 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1011 - 1014.

14
[ 53174-98-4 ]
[ 124168-58-7 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 457 - 465.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 7577 - 7589.

15
[ 53174-98-4 ]
[ 124168-21-4 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 457 - 465.

16
[ 53174-98-4 ]
[ 124168-24-7 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 457 - 465.

17
[ 6926-58-5 ]
[ 53174-98-4 ]
[ 1035162-89-0 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 3048 - 3064.

18
[ 79-19-6 ]
[ 53174-98-4 ]
[ 1035162-87-8 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 3048 - 3064.

19
[ 53174-98-4 ]
[ 1402598-26-8 ]

References: [1]Patent: WO2012/138776,2012,A1 .

20
[ 53174-98-4 ]
[ 1402598-27-9 ]

References: [1]Patent: WO2012/138776,2012,A1 .

21
[ 53174-98-4 ]
[ 1402598-28-0 ]

References: [1]Patent: WO2012/138776,2012,A1 .

22
[ 53174-98-4 ]
[ 1402598-29-1 ]

References: [1]Patent: WO2012/138776,2012,A1 .

23
[ 53174-98-4 ]
[ 1402598-30-4 ]

References: [1]Patent: WO2012/138776,2012,A1 .

24
[ 874842-53-2 ]
[ 53174-98-4 ]
[ 1402599-37-4 ]

Yield	Reaction Conditions	Operation in experiment
	With Montmorillonite K 10; In toluene; for 5h;Reflux;	A 100 mL round-bottomed flask was charged with thieno[2,3-b]pyridine- 2-carbaldehyde (1.0 g, 6.1 mmol, Maybridge, Tintagel, United Kingdom), 3,4- dihydro-2H-l,5-benzodioxepine-7-sulfonamide (1.4 g, 6.1 mmol, Enamine, Kiev, Ukraine), Montmorillonite K 10 (1.4 g, Sigma- Aldrich, St. Louis, MO), and toluene (31 mL), fitted with a Dean-Stark trap and a reflux condenser, and then the reaction mixture was heated at reflux for 5 h. After that time, the reaction mixture was filtered, the filtrate was allowed to cool to room temperature, filtered, and the filter cake was collected to give N-(thieno[2,3-b]pyridin-2- ylmethylidene)-3,4-dihydro-2H-l,5-benzodioxepine-7-sulfonamide (1.1 g) as pale, peach-colored solid.

References: [1]Patent: WO2012/138776,2012,A1 .Location in patent: Page/Page column 142-143.

25
[ 1351282-48-8 ]
[ 53174-98-4 ]
[ 1351929-87-7 ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium metabisulfite; In water; isopropyl alcohol; at 170.0℃; for 0.166667h;Microwave irradiation;	A mixture of 4-(2-(Pyridin-4-yl)-1H-benzo[d]imidazol-5-yl)benzene-1,2-diamine (intermediate A) (50 mg, 0.17 mmol), <strong>[53174-98-4]thieno[2,3-b]pyridine-2-carbaldehyde</strong> (33 mg, 0.20 mmol) and Na2S2O5 (38 mg. 0.20 mmol) in IPA-H2O (3:1, 8 mL) was heated under microwave radiation for 170 C. for 10 min. The mixture was absorbed onto silica and purified by column chromatography eluting with (95:5 EtOAc-MeOH to 85:15 EtOAc-MeOH) afforded the title compound as a yellow solid (30 mg, 0.07mmol, 40%).[0324]LCMS RT=1.38min, MH+ 445.1; 1H NMR (MeOD): 8.74 (2H, dd, J 4.7 and 1.6), 8.58 (1H, dd, J 4.7 and 1.6), 8.31 (1H, dd, J 8.1 and 1.6), 8.10 (2H, dd, J 4.7 and 1.6), 7.78 (1H, s), 7.90-7.62 (6H, m) and 7.48 (1H, dd, J 8.1 and 4.7).

References: [1]Patent: US2013/95057,2013,A1 .Location in patent: Paragraph 0323-0324.

26
N-[4-(trans-2-aminocyclopropyl)phenyl]-3-(trifluoromethyl)benzamide hydrochloride [ No CAS ]
[ 53174-98-4 ]
N-(4-{trans-2-[(thieno[2,3-b]pyridin-2-ylmethyl)amino]cyclopropyl}phenyl)-3-(trifluoromethyl)benzamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 161 N-(4-{trans-2-[(thieno[2,3-b]pyridin-2-ylmethyl)amino]cyclopropyl}phenyl)-3-(trifluoromethyl)benzamide hydrochloride By a method similar to Example 65, the title compound (10 mg) was obtained from N-[4-(trans-2-aminocyclopropyl)phenyl]-3-(trifluoromethyl)benzamide hydrochloride (75 mg) and <strong>[53174-98-4]thieno[2,3-b]pyridine-2-carbaldehyde</strong> (44.6 mg). MS (API+): [M+H]+ 468.0. 1H NMR (300 MHz, CD3OD) delta 1.36-1.57 (2H, m), 2.41 (1H, ddd, J = 10.2, 6.5, 3.7 Hz), 3.01 (1H, dt, J = 7.6, 4.0 Hz), 4.73 (2H, s), 7.07 (2H, d, J = 8.7 Hz), 7.44-7.54 (2H, m), 7.61 (2H, d, J = 8.7 Hz), 7.70-7.79 (1H, m), 7.90 (1H, d, J = 7.9 Hz), 8.15-8.30 (3H, m), 8.58 (1H, dd, J = 4.7, 1.5 Hz).

References: [1]Patent: EP2743256,2014,A1 .Location in patent: Page/Page column.

27
[ 53174-98-4 ]
[ 1313722-59-6 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7577 - 7589.

Historical Records

Technical Information

? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs 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 ? 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 ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Related Functional Groups of
[ 53174-98-4 ]

Aldehydes

A119178 [1011-40-1]

2-Phenylthiazole-5-carbaldehyde

Similarity: 0.81

A149755 [198904-53-9]

4-(Thiazol-2-yl)benzaldehyde

Similarity: 0.73

A275311 [885465-97-4]

3-Thiazol-2-yl-benzaldehyde

Similarity: 0.73

A122905 [223575-69-7]

2-(Thiazol-2-yl)benzaldehyde

Similarity: 0.71

A120208 [914348-82-6]

2-(4-Methoxyphenyl)thiazole-5-carbaldehyde

Similarity: 0.70

Related Parent Nucleus of
[ 53174-98-4 ]

Other Aromatic Heterocycles

A221827 [59944-76-2]

Thieno[2,3-b]pyridine-2-carboxylic acid

Similarity: 0.89

A463349 [58327-75-6]

3-Aminothieno[2,3-b]pyridine-2-carboxylic acid

Similarity: 0.75

A106761 [937640-24-9]

3-Chlorothieno[2,3-b]pyridine-2-carboxylic acid

Similarity: 0.74

A553194 [111042-89-8]

Methyl 3-aminothieno[2,3-b]pyridine-2-carboxylate

Similarity: 0.73

A165936 [21344-24-1]

5-Bromothieno[2,3-b]pyridine

Similarity: 0.71

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H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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

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