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

HRID 453312Notes

Reaction equation

HRID 453312 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:13]=[C:14]3[N:20]=[C:19]([C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[NH2:23])[S:18][C:15]3=[N:16][CH:17]=2)[CH2:7][CH2:6]1.[CH3:28][C:29]1[O:33][C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:31][C:30]=1[C:40](O)=[O:41]>>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:13]=[C:14]3[N:20]=[C:19]([C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[NH:23][C:40]([C:30]4[N:31]=[C:32]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[O:33][C:29]=4[CH3:28])=[O:41])[S:18][C:15]3=[N:16][CH:17]=2)[CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 3185335-Methyl-2-phenyl-1,3-oxazole-4-carboxylic acidHCID 585518702-(6-((4-(2-Methoxyethyl)piperazin-1-yl)methyl)thiazolo[5,4-b]pyridin-2-yl)aniline

Product 1

HCID 46244963N-(2-(6-((4-(2-methoxyethyl)piperazin-1-yl)methyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-5-methyl-2-phenyloxazole-4-carboxamide

Procedure

The title compound was prepared according to amide synthesis general method B, utilizing 2-(6-((4-(2-methoxyethyl)piperazin-1-yl)methyl)thiazolo[5,4-b]pyridin-2-yl)aniline and 5-methyl-2-phenyloxazole-4-carboxylic acid (1.5 eq). The product precipitated from the reaction mixture, and was filtered and chased with methanol. The product was purified by prep HPLC. MS Calcd for C31H32N6O3S: 568.23. Found (M+H)+ m/z=569.

Workup

  1. customThe product precipitated from the reaction mixture
  2. filtrationwas filtered
  3. customThe product was purified by prep HPLC

Sources & evidence

ORD record
ord-dbfdb232903c4b31b552446631a67621
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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