(5-Fluoropyridin-3-yl)methanamine → 4-methyl-N-((6-methylpyrazin-2-yl)methyl)-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxamide
Reaction equation
FC1C=C(CN)C=NC=1.[CH3:10][C:11]1[N:16]=[C:15]([CH2:17][NH2:18])[CH:14]=[N:13][CH:12]=1.[CH3:19][C:20]1[N:21]=[C:22]([N:28]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][C:36]([F:39])([F:38])[F:37])[C:29]2=[O:40])[S:23][C:24]=1[C:25](O)=[O:26]>>[CH3:19][C:20]1[N:21]=[C:22]([N:28]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][C:36]([F:37])([F:38])[F:39])[C:29]2=[O:40])[S:23][C:24]=1[C:25]([NH:18][CH2:17][C:15]1[CH:14]=[N:13][CH:12]=[C:11]([CH3:10])[N:16]=1)=[O:26]Participants
Reactant 3
Product 1
Procedure
Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with (6-methylpyrazin-2-yl)methanamine 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 34% yield: mp 123-123° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.51 (s, 1H), 8.39 (s, 1H), 6.75-6.72 (m, 1H), 4.70 (d, J=4.9 Hz, 2H), 4.17-4.12 (m, 2H), 3.64-3.59 (m, 2H), 3.44-3.39 (m, 2H), 2.63 (s, 3H), 2.57 (s, 3H), 2.25-2.09 (m, 2H), 1.92-1.82 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 162.5, 157.4, 155.6, 152.9, 152.6, 148.7, 143.4, 142.7, 128.6, 124.9, 117.6, 42.9, 42.3, 42.0, 31.4, 30.9, 21.2, 20.2, 20.1, 17.3; MS (ES+) m/z 442.7 (M+1).
Sources & evidence
- ORD record
- ord-daeac39823f94fdabb1a30c704d93657
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318949B2
Reaction notes
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