Benzyl Bromide → N-benzyl-2-(3-benzyl-2-oxopiperidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 883154Notes

Reaction equation

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

Participants

Reactant 2

HCID 7498Benzyl Bromide

HCID 24799232N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 24800980N-benzyl-2-(3-benzyl-2-oxopiperidin-1-yl)-4-methylthiazole-5-carboxamideYield 26%

Procedure

Following the procedure as described in Example 2, making variation as required to use N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide in place of N-(4-fluorobenzyl)-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide to react with (bromomethyl)benzene in place of 1-(bromomethyl)-4-(trifluoromethyl)benzene, the title compound was obtained as a white solid in 26% yield: mp 162-164° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.39-7.32 (m, 10H), 6.01 (br s, 1H), 4.57 (d, J=5.3 Hz, 2H), 4.32-4.18 (m, 1H), 4.02-3.88 (m, 1H), 3.47-3.38 (m, 1H), 2.87-2.69 (m, 2H), 2.64 (s, 3H), 2.07-1.45 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 172.2, 162.7, 157.0, 152.2, 138.9, 137.9, 129.2, 128.8, 128.6, 127.9, 127.7, 126.5, 119.4, 48.1, 44.1, 44.0, 37.6, 24.8, 21.2, 17.4; MS (ES+) m/z 420.5 (M+1).

Sources & evidence

ORD record: ord-8d121ecbb4b14e5b858b7747dc7e80a7
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236835B2

Reaction notes

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