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

HRID 554999Notes

Reaction equation

HRID 554999 reaction equation
FC1C=C(CN)C=NC=1.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][NH2:17].[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:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=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 195092-PyridinemethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579199962-(3-Isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579197462-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-2-ylmethyl)thiazole-5-carboxamideYield 46%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with pyridin-2-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 46% yield: 1H NMR (300 MHz, CDCl3) δ 8.52-8.50 (m, 1H), 7.65-7.60 (m, 1H), 7.26-7.23 (m, 1H), 7.18-7.14 (m, 1H), 7.11-7.06 (m, 1H), 4.66 (d, J=5.6 Hz, 2H), 4.10-4.05 (m, 2H), 3.58-3.53 (m, 2H), 3.09 (d, J=7.5 Hz, 2H), 2.61 (s, 3H), 1.94-1.85 (m, 1H), 0.91 (d, J=6.4 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ162.5, 157.6, 155.8, 155.6, 152.3, 148.8, 136.5, 122.2, 121.7, 117.7, 51.4, 44.5, 42.7, 41.9, 26.6, 19.8, 17.1; MS (ES+) m/z 373.8 (M+1).

Sources & evidence

ORD record
ord-001d57b153264f8cb5af296bf3c0fbda
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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