1-[5-Methyl-2-(trifluoromethyl)furan-3-yl]methanamine → HCID 57744444, compound

HRID 1887354Notes

Reaction equation

HRID 1887354 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([F:10])([F:9])[F:8])=[C:4]([CH2:11][NH2:12])[CH:3]=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:12][CH2:11][C:4]3[CH:3]=[C:2]([CH3:1])[O:6][C:5]=3[C:7]([F:10])([F:8])[F:9])=[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 27799001-[5-Methyl-2-(trifluoromethyl)furan-3-yl]methanamineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 57744444HCID 57744444, compoundYield 28%

Procedure

Following the procedure as described in Example 22, making variation only as required to use (5-methyl-2-(trifluoromethyl)furan-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 28% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.75 (t, J=5.7 Hz, 1H), 8.61 (d, J=8.1 Hz, 1H), 7.52-7.30 (m, 5H), 6.39 (dd, J=8.1, 2.7 Hz, 1H), 6.26 (s, 1H), 6.23 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.30 (d, J=5.7 Hz, 2H), 2.53 (m, 3H), 2.26 (m, 3H); MS (ES+) m/z 504.2 (M+1).

Sources & evidence

ORD record
ord-cc4e892c650c4570acb8d735c4c43119
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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