2-Pyridinemethanamine → 4-methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)-N-(pyridin-2-ylmethyl)thiazole-5-carboxamide

HRID 1882453Notes

Reaction equation

HRID 1882453 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].[CH3:18][C:19]1[N:20]=[C:21]([N:27]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34][C:35]([F:38])([F:37])[F:36])[C:28]2=[O:39])[S:22][C:23]=1[C:24](O)=[O:25]>>[CH3:18][C:19]1[N:20]=[C:21]([N:27]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34][C:35]([F:36])([F:37])[F:38])[C:28]2=[O:39])[S:22][C:23]=1[C:24]([NH:17][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=1)=[O:25]

Participants

4

Reactant 3

HCID 195092-PyridinemethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198994-Methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

Product 1

HCID 579199744-methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)-N-(pyridin-2-ylmethyl)thiazole-5-carboxamideYield 28%

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 4-methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-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 28% yield: 1H NMR (300 MHz, CDCl3) δ 8.56-8.54 (m, 1H), 7.70-7.64 (m, 1H), 7.30-7.19 (m, 2H), 7.13-7.10 (m, 1H), 4.69 (d, J=4.6 Hz, 2H), 4.17-4.11 (m, 2H), 3.63-3.58 (m, 2H), 2.65 (s, 3H), 2.24-2.08 (m, 2H), 1.92-1.75 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 162.5, 157.5, 155.8, 155.6, 152.3, 148.9, 136.7, 122.4, 121.9, 118.2, 44.6, 42.9, 42.3, 42.0, 31.8, 31.4, 30.9, 30.6, 20.2, 20.1, 17.3; MS (ES+) m/z 427.9 (M+1).

Sources & evidence

ORD record
ord-656c556f77fb48fa991f73ae6f9250a2
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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