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

HRID 453316Notes

Reaction equation

HRID 453316 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.[C:28]1([C:34]2[O:35][C:36]([C:42]([F:45])([F:44])[F:43])=[C:37]([C:39](O)=[O:40])[N:38]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[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:39]([C:37]4[N:38]=[C:34]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[O:35][C:36]=4[C:42]([F:44])([F:45])[F:43])=[O:40])[S:18][C:15]3=[N:16][CH:17]=2)[CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 585518702-(6-((4-(2-Methoxyethyl)piperazin-1-yl)methyl)thiazolo[5,4-b]pyridin-2-yl)aniline

Product 1

HCID 46245208N-(2-(6-((4-(2-methoxyethyl)piperazin-1-yl)methyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-2-phenyl-5-(trifluoromethyl)oxazole-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 2-phenyl-5-(trifluoromethyl)oxazole-4-carboxylic acid (1.5 eq). The product was filtered from the crude reaction mixture, evaporated with methanol, and purified by silica gel chromatography (gradient 0 to 10% methanol in CH2Cl2) and by prep HPLC. MS Calcd for C31H29F3N6O3S: 622.20. Found (M+H)+ m/z=623.

Workup

  1. filtrationThe product was filtered from the crude
  2. customreaction mixture
  3. customevaporated with methanol
  4. custompurified by silica gel chromatography (gradient 0 to 10% methanol in CH2Cl2) and by prep HPLC

Sources & evidence

ORD record
ord-0a043c69164646249fb9d4c4cc1b6015
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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