5-(Aminomethyl)-2-(trifluoromethyl)pyridine → HCID 57744473, compound

HRID 1887369Notes

Reaction equation

HRID 1887369 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][N:24]([C:27]2[S:28][C:29]([C:33](O)=[O:34])=[C:30]([CH3:32])[N:31]=2)[C:23](=[O:36])[CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][N:24]([C:27]2[S:28][C:29]([C:33]([NH:10][CH2:9][C:6]3[CH:7]=[N:8][C:3]([C:2]([F:11])([F:1])[F:12])=[CH:4][CH:5]=3)=[O:34])=[C:30]([CH3:32])[N:31]=2)[C:23](=[O:36])[CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 57744473HCID 57744473, compoundYield 38%

Procedure

Following the procedure as described in Example 22, making variation only as required to use (6-(trifluoromethyl)pyridin-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 38% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.89 (t, J=5.6 Hz, 1H), 8.69 (br s, 1H), 8.61 (d, J=8.1 Hz 1H), 7.98-7.96 (m, 1H), 7.87-7.84 (m, 1H), 7.45-7.33 (m, 5H), 6.39 (dd, J=8.1, 2.6 Hz, 1H), 6.23 (d, J=2.6 Hz, 1H), 5.16 (s, 2H), 4.50 (d, J=5.6 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 501.1 (M+1).

Sources & evidence

ORD record
ord-1dec8c1769604eda8d24a97c59580c6e
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…