1-Hydroxybenzotriazole → 2-(3-chlorothiophen-2-yl)-3-methyl-6-trifluoromethylthio-3H-imidazo[4,5,b]pyridine

HRID 2272918Notes

Reaction equation

HRID 2272918 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([S:10][C:11]([F:14])([F:13])[F:12])=[CH:5][N:4]=1.[Cl:15][C:16]1[CH:20]=[CH:19][S:18][C:17]=1[C:21](O)=O.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>O.N1C=CC=CC=1>[Cl:15][C:16]1[CH:20]=[CH:19][S:18][C:17]=1[C:21]1[N:2]([CH3:1])[C:3]2=[N:4][CH:5]=[C:6]([S:10][C:11]([F:13])([F:12])[F:14])[CH:7]=[C:8]2[N:9]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 7012693-Chlorothiophene-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68091243N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine

Product 1

HCID 1179741442-(3-chlorothiophen-2-yl)-3-methyl-6-trifluoromethylthio-3H-imidazo[4,5,b]pyridineYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.50 g of N2-methyl-5-trifluoromethylthiopyridine-2,3-diamine, 0.44 g of 3-chloro-thiophene-2-carboxylic acid, 0.51 g of EDCI hydrochloride, 30 mg of HOBt and 5 ml of pyridine was stirred at 90° C. for 10 hours. Water was poured into the cooled reaction mixture, and the deposited precipitate was filtered. The filtrate was applied to a silica gel column chromatography to obtain 0.7 g of 2-(3-chlorothiophen-2-yl)-3-methyl-6-trifluoromethylthio-3H-imidazo[4,5,b]pyridine.

Workup

  1. filtrationthe deposited precipitate was filtered

Sources & evidence

ORD record
ord-7f672f5555d2422298167e4685bbed44
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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