4-(Trifluoromethyl)benzylamine → HCID 24801504, compound

HRID 883166Notes

Reaction equation

HRID 883166 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[CH2:13]([NH:20][C:21]([C:23]1[S:27][C:26]([N:28]2[CH2:33][CH2:32][CH2:31][CH:30](Br)[C:29]2=[O:35])=[N:25][C:24]=1[CH3:36])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([NH:20][C:21]([C:23]1[S:27][C:26]([N:28]2[CH2:33][CH2:32][CH2:31][CH:30]([NH:10][CH2:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:11])([F:12])[F:1])=[CH:8][CH:7]=3)[C:29]2=[O:35])=[N:25][C:24]=1[CH3:36])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 768044-(Trifluoromethyl)benzylamineHCID 24799235HCID 24799235, compound

Product 1

HCID 24801504HCID 24801504, compoundYield 20%

Procedure

Following the procedure as described in Example 5, making variation as required to use (4-(trifluoromethyl)phenyl)methanamine in place of 2-cyclopropylethanamine to react with N-benzyl-2-(3-bromo-2-oxopiperidin-1-yl)-4-methylthiazole-5-carboxamide in place of 2-(3-bromo-2-oxopyrrolidin-1-yl)-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 20% yield: mp 39-40° C. (diethyl ether); 1H NMR (300 MHz, CDCl3) δ 7.55 (d, J=8.1 Hz, 2H), 7.45 (d, J=8.1 Hz, 2H), 7.39-7.21 (m, 5H), 6.03 (t, J=5.6 Hz, 1H), 4.55 (d, J=5.6 Hz, 2H), 4.32-4.21 (m, 1H), 4.06-3.96 (m, 1H), 3.93 (s, 2H), 3.50-3.39 (m, 1H), 2.62 (s, 3H), 2.30-2.05 (m, 2H), 1.99-1.83 (m, 2H), 1.81-1.66 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 171.4, 162.5, 156.6, 152.0, 143.8, 137.9, 129.4, 128.8, 128.3, 127.9, 127.7, 125.5, 125.4, 119.7, 57.9, 50.9, 47.5, 44.1, 26.5, 20.4, 17.4; MS (ES+) m/z 503.3 (M+1).

Sources & evidence

ORD record
ord-1512150c533247919fa95b7394e00629
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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