(4-methylthiophen-2-yl)methanamine → HCID 57744514, compound

HRID 1887357Notes

Reaction equation

HRID 1887357 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:7][NH2:8])[S:5][CH: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:4]3[S:5][CH:6]=[C:2]([CH3:1])[CH:3]=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 2795528(4-methylthiophen-2-yl)methanamineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 57744514HCID 57744514, compoundYield 46%

Procedure

Following the procedure as described in Example 22, making variation only as required to use (4-methylthiophen-2-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 46% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.83 (t, J=5.8 Hz, 1H), 8.60 (d, J=8.1 Hz, 1H), 7.50-7.31 (m, 5H), 6.91 (s, 1H), 6.77 (s, 1H), 6.38 (dd, J=8.1, 2.6 Hz, 1H), 6.22 (d, J=2.6 Hz, 1H), 5.15 (s, 2H), 4.46 (d, J=5.7 Hz, 2H), 2.53 (s, 3H), 2.12 (s, 3H); MS (ES+) m/z 452.2 (M+1).

Sources & evidence

ORD record
ord-2095e805c8da472e9d0bcd9ef7ea9e76
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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