4-Phenylthiazole-2-carboxylic acid → 4-phenyl-N-(2-(6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-2-carboxamide

HRID 453308Notes

Reaction equation

HRID 453308 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[NH2:18])[S:13][C:10]3=[N:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23]1([C:29]2[N:30]=[C:31]([C:34](O)=[O:35])[S:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[C:23]1([C:29]2[N:30]=[C:31]([C:34]([NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:14]3[S:13][C:10]4[C:9]([N:15]=3)=[CH:8][C:7]([CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:12][N:11]=4)=[O:35])[S:32][CH:33]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 38785394-Phenylthiazole-2-carboxylic acidHCID 585518882-(6-(Pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)aniline

Product 1

HCID 585518974-phenyl-N-(2-(6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared according to amide synthesis general method A, utilizing 2-(6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)aniline and 4-phenylthiazole-2-carboxylic acid. The product was isolated by precipitation by the addition of water, triturated with hot methanol and purified by silica gel chromatography (gradient 0 to 10% methanol in CH2Cl2). MS Calcd for C27H23N5OS2: 497.13. Found (M+H)+ m/z=498.

Workup

  1. customtriturated with hot methanol
  2. custompurified by silica gel chromatography (gradient 0 to 10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-2016beb5d7fa453c87c266200ed7fa9a
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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