2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid → HCID 178433083, compound

HRID 1887367Notes

Reaction equation

HRID 1887367 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([CH2:6][NH2:7])=[N:2]1.[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>>[NH:1]1[CH:5]=[CH:4][C:3]([CH2:6][NH:7][C:28]([C:24]2[S:23][C:22]([N:19]3[CH:20]=[CH:21][C:16]([O:15][CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:17][C:18]3=[O:31])=[N:26][C:25]=2[CH3:27])=[O:29])=[N:2]1

Participants

3

Reactant 2

HCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acidHCID 178510230HCID 178510230, compound

Product 1

HCID 178433083HCID 178433083, compoundYield 43%

Procedure

Following the procedure as described in Example 22, making variation only as required to use (1H-pyrazol-3-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 43% yield: 1H NMR (300 MHz, DMSO-d6) δ 12.63 (br s, 1H), 8.74-8.54 (m, 2H), 7.63-7.31 (m, 6H), 6.38 (dd, J=8.1, 2.5 Hz, 1H), 6.22 (d, J=2.5 Hz, 1H), 6.13 (d, J=1.0 Hz, 1H), 5.15 (s, 2H), 4.37 (d, J=5.6 Hz, 2H), 2.53 (s, 3H); MS (ES+) m/z 422.2 (M+1).

Sources & evidence

ORD record
ord-3853ffd482754c3dba5d04f2211ebb95
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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