3,3,3-Trifluoropropylamine → N-(4-fluorobenzyl)-4-methyl-2-(2-oxo-3-(3,3,3-trifluoropropylamino)pyrrolidin-1-yl)thiazole-5-carboxamide

HRID 883165Notes

Reaction equation

HRID 883165 reaction equation
[F:1][C:2]([F:7])([F:6])[CH2:3][CH2:4][NH2:5].Br[CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]([C:20]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[O:21])=[C:17]([CH3:19])[N:18]=2)[C:10]1=[O:31]>>[F:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][NH:22][C:20]([C:16]2[S:15][C:14]([N:11]3[CH2:12][CH2:13][CH:9]([NH:5][CH2:4][CH2:3][C:2]([F:7])([F:6])[F:1])[C:10]3=[O:31])=[N:18][C:17]=2[CH3:19])=[O:21])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 100013,3,3-TrifluoropropylamineHCID 247992342-(3-bromo-2-oxopyrrolidin-1-yl)-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide

Product 1

HCID 24801836N-(4-fluorobenzyl)-4-methyl-2-(2-oxo-3-(3,3,3-trifluoropropylamino)pyrrolidin-1-yl)thiazole-5-carboxamideYield 19%

Procedure

Following the procedure as described in Example 5, making variation as required to use 3,3,3-trifluoropropan-1-amine in place of 2-cyclopropylethanamine to react with 2-(3-bromo-2-oxopyrrolidin-1-yl)-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 19% yield: mp 142-143° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.35 (m, 2H), 7.07-6.93 (m, 2H), 6.00 (br s, 1H), 4.51 (d, J=5.4 Hz, 2H), 4.29-4.16 (m, 1H), 3.65-3.81 (m, 1H), 3.76-3.64 (m, 1H), 3.15-3.02 (m, 1H), 2.98-2.85 (m, 1H), 2.61 (s, 3H), 2.60-2.48 (m, 1H), 2.43-2.22 (m, 2H), 2.08-1.89 (m, 1H), 1.79 (br s, 1H); MS (ES+) m/z 445.3 (M+1).

Sources & evidence

ORD record
ord-56634bf71f3f4a57b5d85d282f7d34bc
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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