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

HRID 1799124Notes

Reaction equation

HRID 1799124 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[C:10]3[N:16]=[C:15]([C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[NH2:19])[S:14][C:11]3=[N:12][CH:13]=2)[CH2:3][CH2:2]1.[CH3:24][C:25]1[O:29][C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:27][C:26]=1[C:36](O)=[O:37]>O>[CH3:24][C:25]1[O:29][C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:27][C:26]=1[C:36]([NH:19][C:18]1[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=1[C:15]1[S:14][C:11]2[C:10]([N:16]=1)=[CH:9][C:8]([CH2:7][N:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)=[CH:13][N:12]=2)=[O:37]

Participants

4

Reactant 2

HCID 3185335-Methyl-2-phenyl-1,3-oxazole-4-carboxylic acidHCID 585518812-(6-(Morpholinomethyl)thiazolo[5,4-b]pyridin-2-yl)aniline

Product 1

HCID 462452095-methyl-N-(2-(6-(morpholinomethyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-2-phenyloxazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared according to amide synthesis general method A, utilizing 2-(6-(morpholinomethyl)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 C28H25N5O3S: 511.17. Found (M+H)+ m/z=512.

Workup

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

Sources & evidence

ORD record
ord-abbb3ea6402441489b7871c0d9bd371d
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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