2-Fluorobenzylamine → 2-(3-benzyl-2-oxoimidazolidin-1-yl)-N-(2-fluorobenzyl)-4-methylthiazole-5-carboxamide

HRID 560632Notes

Reaction equation

FC1C=CC(CN)=CC=1.[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14].[CH2:19]([N:26]1[CH2:30][CH2:29][N:28]([C:31]2[S:32][C:33]([C:37](O)=[O:38])=[C:34]([CH3:36])[N:35]=2)[C:27]1=[O:40])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([N:26]1[CH2:30][CH2:29][N:28]([C:31]2[S:32][C:33]([C:37]([NH:14][CH2:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[F:10])=[O:38])=[C:34]([CH3:36])[N:35]=2)[C:27]1=[O:40])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 3

HCID 666492-Fluorobenzylamine

HCID 673264-Fluorobenzylamine

HCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 594812562-(3-benzyl-2-oxoimidazolidin-1-yl)-N-(2-fluorobenzyl)-4-methylthiazole-5-carboxamideYield 44%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 4-fluorobenzylamine with 2-fluorobenzylamine to react with 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white powder in 44% yield: mp 167-168° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.39-7.20 (m, 7H), 7.11-7.00 (m, 2H), 6.03 (s, 1H), 4.59 (d, J=5.7 Hz, 2H), 4.45 (s, 2H), 4.07-4.00 (m, 2H), 3.46-3.40 (m, 2H), 2.58 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.4, 159.4 157.4, 155.4, 153.0, 135.5, 130.3, 129.4, 129.3, 128.9, 125.4, 124.4, 117.2, 115.5, 115.8, 47.9, 42.0, 41.6, 38.7, 17.1; MS (ES+) m/z 425.2 (M+1).

Sources & evidence

ORD record: ord-1f90c733bc5142ca8549d77097851e01
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

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