(2-Methylthiazol-4-yl)MethanaMine → 2-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-N-((2-Methylthiazol-4-yl)methyl)thiazole-5-carboxamide

HRID 1887361Notes

Reaction equation

HRID 1887361 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][NH2:8])[N:6]=1.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([C:23]2[S:24][C:25]([C:29](O)=[O:30])=[C:26]([CH3:28])[N:27]=2)[C:19](=[O:32])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([C:23]2[S:24][C:25]([C:29]([NH:8][CH2:7][C:5]3[N:6]=[C:2]([CH3:1])[S:3][CH:4]=3)=[O:30])=[C:26]([CH3:28])[N:27]=2)[C:19](=[O:32])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 18467479(2-Methylthiazol-4-yl)MethanaMineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 577444512-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-N-((2-Methylthiazol-4-yl)methyl)thiazole-5-carboxamideYield 74%

Procedure

Following the procedure as described in Example 25, making variation only as required to use (2-methylthiazol-4-yl)methanamine 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 74% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.74 (t, J=5.7 Hz, 1H), 8.61 (d, J=8.1 Hz, 1H), 7.45-7.31 (m, 5H), 7.16 (s, 1H), 6.38 (dd, J=8.1, 2.7 Hz, 1H), 6.23 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.42 (d, J=5.7 Hz, 2H), 2.59 (s, 3H), 2.54 (s, 3H); MS (ES+) m/z 453.1 (M+1).

Sources & evidence

ORD record
ord-af854870d1e846e983cd9c61b0b9aaba
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…