1-Benzothiophen-2-ylmethylamine → 2-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-N-((5-methylthiophen-2-yl)methyl)thiazole-5-carboxamide

HRID 1887356Notes

Reaction equation

HRID 1887356 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH2:7][NH2:8])=[CH:4][CH:3]=1.S1C(CN)=CC2C=CC=CC1=2.[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][N:31]([C:34]2[S:35][C:36]([C:40](O)=[O:41])=[C:37]([CH3:39])[N:38]=2)[C:30](=[O:43])[CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][N:31]([C:34]2[S:35][C:36]([C:40]([NH:8][CH2:7][C:5]3[S:6][C:2]([CH3:1])=[CH:3][CH:4]=3)=[O:41])=[C:37]([CH3:39])[N:38]=2)[C:30](=[O:43])[CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 2370741-Benzothiophen-2-ylmethylamineHCID 4313442(5-Methylthiophen-2-yl)methanamineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 577444832-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-N-((5-methylthiophen-2-yl)methyl)thiazole-5-carboxamideYield 43%

Procedure

Following the procedure as described in Example 22, making variation only as required to use (5-methylthiophen-2-yl)methanamine in replace of benzo[b]thiophen-2-ylmethanamine to react with 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 43% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.82 (t, J=5.8 Hz, 1H), 8.60 (d, J=8.1 Hz, 1H), 7.45-7.30 (m, 5H), 6.73 (d, J=3.3 Hz, 1H), 7.59-6.57 (m, 1H), 6.38 (dd, J=8.1, 2.7 Hz, 1H), 6.22 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.43 (d, J=5.8 Hz, 2H), 2.53 (s, 3H), 2.34 (s, 3H); MS (ES+) m/z 452.1 (M+1).

Sources & evidence

ORD record
ord-e14c289add4a421991ae4604ed5b8053
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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