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

HRID 555003Notes

Reaction equation

HRID 555003 reaction equation
FC1C=C(CN)C=NC=1.[O:10]1[CH:14]=[C:13]([CH2:15][NH2:16])[N:12]=[CH:11]1.[CH2:17]([N:21]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28]([C:32](O)=[O:33])=[C:29]([CH3:31])[N:30]=2)[C:22]1=[O:35])[CH:18]([CH3:20])[CH3:19]>>[CH2:17]([N:21]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28]([C:32]([NH:16][CH2:15][C:13]3[N:12]=[CH:11][O:10][CH:14]=3)=[O:33])=[C:29]([CH3:31])[N:30]=2)[C:22]1=[O:35])[CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 230556901,3-Oxazol-4-ylmethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579199962-(3-Isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579199802-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methyl-N-(oxazol-4-ylmethyl)thiazole-5-carboxamideYield 17%

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-isobutyl-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 17% yield: mp 115-118° C.; 1H NMR (300 MHz, CDCl3) δ7.85 (s, 1H), 7.64 (s, 1H), 6.36-6.32 (m, 1H), 4.47 (d, J=5.5 Hz, 2H), 4.11-4.06 (m, 2H), 3.59-3.54 (m, 2H), 3.09 (d, J=7.4 Hz, 2H), 2.56 (s, 3H), 1.97-1.83 (m, 1H), 0.91 (d, J=7.4 Hz, 6H); MS (ES+) m/z 377.1 (M+1).

Sources & evidence

ORD record
ord-da11b355ac7147efb39d0be48dac230f
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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