4-Pyridinemethanamine → 2-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-4-ylmethyl)thiazole-5-carboxamide

HRID 554997Notes

Reaction equation

HRID 554997 reaction equation
FC1C=C(CN)C=NC=1.[N:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[CH:12][CH:11]=1.[CH2:18]([N:22]1[CH2:26][CH2:25][N:24]([C:27]2[S:28][C:29]([C:33](O)=[O:34])=[C:30]([CH3:32])[N:31]=2)[C:23]1=[O:36])[CH:19]([CH3:21])[CH3:20]>>[CH2:18]([N:22]1[CH2:26][CH2:25][N:24]([C:27]2[S:28][C:29]([C:33]([NH:17][CH2:16][C:13]3[CH:14]=[CH:15][N:10]=[CH:11][CH:12]=3)=[O:34])=[C:30]([CH3:32])[N:31]=2)[C:23]1=[O:36])[CH:19]([CH3:21])[CH3:20]

Participants

4

Reactant 3

HCID 773174-PyridinemethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579199962-(3-Isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579199472-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-4-ylmethyl)thiazole-5-carboxamideYield 48%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with pyridin-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 48% yield: mp 185-187° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CD3OD) δ 8.49-8.47 (m, 2H), 7.40-7.38 (d, J=7.4 Hz, 1H), 4.55 (s, 2H), 4.14-4.07 (m, 2H), 3.68-3.63 (m, 2H), 3.12 (d, J=7.5 Hz, 2H), 2.55 (s, 3H), 2.02-1.93 (m, 1H), 0.95 (d, J=6.6 Hz, 6H); MS (ES+) m/z 373.8 (M+1).

Sources & evidence

ORD record
ord-24f699458de24b3fbe88b5907b41ff10
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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