4-Fluorobenzyl bromide → N-(4-fluorobenzyl)-2-(3-(4-fluorobenzyl)-2-oxopyrrolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 883144Notes

Reaction equation

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

Participants

Reactant 2

HCID 680214-Fluorobenzyl bromide

HCID 16954475HCID 16954475, compound

Product 1

HCID 24801506N-(4-fluorobenzyl)-2-(3-(4-fluorobenzyl)-2-oxopyrrolidin-1-yl)-4-methylthiazole-5-carboxamideYield 36%

Procedure

Following the procedure as described in Example 2, making variation as required to use 1-(bromomethyl)-4-fluorobenzene in place of 1-(bromomethyl)-4-(trifluoromethyl)benzene to react with N-(4-fluorobenzyl)-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a white solid in 36% yield: mp 196-197° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.31-7.26 (m, 2H), 7.13 (dd, J=8.6, 5.6 Hz, 2H), 7.06-6.90 (m, 4H), 6.03 (t, J=5.6 Hz, 1H), 4.52 (d, J=5.6 Hz, 2H), 4.06-3.95 (m, 1H), 3.95-3.70 (m, 1H), 3.29-3.10 (m, 1H), 3.05-2.92 (m, 1H), 2.88-2.70 (m, 1H), 2.60 (s, 3H), 2.32-2.17 (m, 1H), 2.00-1.80 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 174.8, 176.3, 162.3, 161.8, 155.4, 152.9, 133.8, 133.7, 130.4, 129.6, 118.5, 115.7, 115.5, 45.9, 44.4, 43.4, 35.6, 24.2, 17.3; MS (ES+) m/z 442.2 (M+1).

Sources & evidence

ORD record: ord-53a39cd61cab477291750b7fd9650bc2
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236835B2

Reaction notes

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