5-Methyl-2-phenyl-1,3-oxazole-4-carboxylic acid → 5-methyl-2-phenyl-N-(2-(6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)oxazole-4-carboxamide

HRID 1799125Notes

Reaction equation

HRID 1799125 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.[CH3:23][C:24]1[O:28][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:26][C:25]=1[C:35](O)=[O:36]>O>[CH3:23][C:24]1[O:28][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:26][C:25]=1[C:35]([NH:18][C:17]1[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=1[C:14]1[S:13][C:10]2[C:9]([N:15]=1)=[CH:8][C:7]([CH2:6][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)=[CH:12][N:11]=2)=[O:36]

Participants

4

Reactant 2

HCID 3185335-Methyl-2-phenyl-1,3-oxazole-4-carboxylic acidHCID 585518882-(6-(Pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)aniline

Product 1

HCID 462449625-methyl-2-phenyl-N-(2-(6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)oxazole-4-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 5-methyl-2-phenyloxazole-4-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 C28H25N5O2S: 495.17. Found (M+H)+ m/z=496.

Workup

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

Sources & evidence

ORD record
ord-86b42175008949a3ad7a011ebc34c353
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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