1,3-Oxazol-4-ylmethanamine → 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(oxazol-4-ylmethyl)thiazole-5-carboxamide

HRID 554996Notes

Reaction equation

HRID 554996 reaction equation
FC1C=C(CN)C=NC=1.[O:10]1[CH:14]=[C:13]([CH2:15][NH2:16])[N:12]=[CH:11]1.[F:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[CH2:27][CH2:26][N:25]([C:28]3[S:29][C:30]([C:34](O)=[O:35])=[C:31]([CH3:33])[N:32]=3)[C:24]2=[O:37])=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[CH2:27][CH2:26][N:25]([C:28]3[S:29][C:30]([C:34]([NH:16][CH2:15][C:13]4[N:12]=[CH:11][O:10][CH:14]=4)=[O:35])=[C:31]([CH3:33])[N:32]=3)[C:24]2=[O:37])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 230556901,3-Oxazol-4-ylmethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579197992-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579198622-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(oxazol-4-ylmethyl)thiazole-5-carboxamideYield 32%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with oxazol-4-ylmethanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid in place of 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 32% yield: mp 188-191° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.86 (s, 1H), 7.66 (s, 1H), 7.29-7.25 (m, 2H), 7.07-7.01 (m, 2H), 6.21-6.17 (m, 1H), 4.51 (d, J=5.8 Hz, 2H), 4.46 (s, 2H), 4.10-4.05 (m, 2H), 3.48-3.42 (m, 2H) 2.60 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 164.1, 162.4, 160.9, 157.5, 155.3, 152.9, 151.3, 136.8, 135.8, 131.4, 131.3, 130.1, 129.9, 117.5, 115.9, 115.7, 47.3, 41.9, 41.6, 35.6, 17.2; MS (ES+) m/z 416.1 (M+1).

Sources & evidence

ORD record
ord-8fe8d2652c6c4171b100843b3098c3db
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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