p-Xylyl bromide → N-benzyl-4-methyl-2-(3-(4-methylbenzyl)-2-oxopiperidin-1-yl)thiazole-5-carboxamide

HRID 883150Notes

Reaction equation

HRID 883150 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][C:29]([CH3:32])=[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][C:29]([CH3:32])=[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

3

Reactant 2

HCID 7721p-Xylyl bromideHCID 24799232N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 24801155N-benzyl-4-methyl-2-(3-(4-methylbenzyl)-2-oxopiperidin-1-yl)thiazole-5-carboxamideYield 53%

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 1-(bromomethyl)-4-methylbenzene in place of 1-(bromomethyl)-4-(trifluoromethyl)benzene, the title compound was obtained as a white solid in 53% yield: mp 110-113° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.37-7.22 (m, 5H), 7.12-6.99 (m, 4H), 6.09 (t, J=5.6 Hz, 1H), 4.56 (d, J=5.6 Hz, 2H), 4.28-4.19 (m, 1H), 3.99-3.86 (m, 1H), 3.43-3.29 (m, 1H), 2.82-2.66 (m, 2H), 2.63 (s, 3H), 2.29 (s, 3H), 2.06-1.69 (m, 3H), 1.61-1.43 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 172.2, 162.7, 157.0, 152.1, 138.0, 136.1, 135.8, 129.2, 129.1, 128.8, 127.9, 127.6, 119.4, 48.1, 44.2, 44.0, 37.1, 24.8, 21.2, 21.1, 17.4; MS (ES+) m/z 434.3 (M+1).

Sources & evidence

ORD record
ord-98f60b66f2b1423da705ba2244187150
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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