5-(3-Methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylic acid → 5-(3-methoxyprop-1-ynyl)-2-phenyl-N-(2-(6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide
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][O:24][CH2:25][C:26]#[C:27][C:28]1[S:32][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:30][C:29]=1[C:39](O)=[O:40]>>[CH3:23][O:24][CH2:25][C:26]#[C:27][C:28]1[S:32][C:31]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[N:30][C:29]=1[C:39]([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:40]Participants
3
Reactant 2
Product 1
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-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylic acid. The product was isolated using workup 2 and purified by silica gel chromatography (gradient 0 to 10% methanol in CH2Cl2) followed by recrystallization from MeOH to give the title compound (111 mg, 30% yield). MS Calcd for C31H27N5O2S2: 565.16. Found (M+H)+ m/z=566.
Workup
- customThe title compound was prepared
- customThe product was isolated
- custompurified by silica gel chromatography (gradient 0 to 10% methanol in CH2Cl2)
- customfollowed by recrystallization from MeOH
Sources & evidence
- ORD record
- ord-4862709448e14888af1822b71f577d56
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492401B2
Reaction notes
Loading…