1,3-Thiazol-2-ylmethanamine → 2-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-N-(thiazol-2-ylmethyl)thiazole-5-carboxamide

HRID 1887355Notes

Reaction equation

HRID 1887355 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH2:7].[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][N:19]([C:22]2[S:23][C:24]([C:28](O)=[O:29])=[C:25]([CH3:27])[N:26]=2)[C:18](=[O:31])[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][N:19]([C:22]2[S:23][C:24]([C:28]([NH:7][CH2:6][C:2]3[S:1][CH:5]=[CH:4][N:3]=3)=[O:29])=[C:25]([CH3:27])[N:26]=2)[C:18](=[O:31])[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 27565071,3-Thiazol-2-ylmethanamineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 577444882-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-N-(thiazol-2-ylmethyl)thiazole-5-carboxamideYield 71%

Procedure

Following the procedure as described in Example 22, making variation only as required to use thiazol-2-ylmethanamine in place 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 71% yield: 1H NMR (300 MHz, DMSO-d6) δ 9.11 (t, J=5.9 Hz, 1H), 8.61 (d, J=8.1 Hz, 1H), 7.70 (d, J=3.3 Hz, 1H), 7.60 (d, J=3.3 Hz, 1H), 7.45-7.33 (m, 5H), 6.39 (dd, J=8.1, 2.7 Hz, 1H), 6.23 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.66 (d, J=5.9 Hz, 2H), 2.56 (m, 3H); MS (ES+) m/z 439.1 (M+1).

Sources & evidence

ORD record
ord-19f74797bf524cd9860f9bf30785613a
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…