(5-Fluoropyridin-3-yl)methanamine → N-((1H-pyrazol-4-yl)methyl)-4-methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxamide

HRID 554988Notes

Reaction equation

HRID 554988 reaction equation
FC1C=C(CN)[CH:5]=[N:6]C=1.[NH:10]1[CH:14]=[CH:13][C:12](CN)=[N:11]1.[CH3:17][C:18]1[N:19]=[C:20]([N:26]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][C:34]([F:37])([F:36])[F:35])[C:27]2=[O:38])[S:21][C:22]=1[C:23]([OH:25])=O>>[NH:11]1[CH:12]=[C:13]([CH2:5][NH:6][C:23]([C:22]2[S:21][C:20]([N:26]3[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][C:34]([F:37])([F:36])[F:35])[C:27]3=[O:38])=[N:19][C:18]=2[CH3:17])=[O:25])[CH:14]=[N:10]1

Participants

4

Reactant 3

HCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198994-Methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxylic acidHCID 178510230HCID 178510230, compound

Product 1

HCID 66661425N-((1H-pyrazol-4-yl)methyl)-4-methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxamideYield 3%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with (1H-pyrazol-3-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 3% yield: 1H NMR (300 MHz, DMSO-d6) δ 12.58 (s, 1H), 8.34-8.32 (m, 1H), 7.58-7.57 (m, 1H), 6.14 (s, 1H), 4.37 (d, J=5.5 Hz, 2H), 4.02-3.96 (m, 2H), 3.59-3.53 (m, 2H), 3.33-3.28 (m, 2H), 2.46 (s, 3H), 2.32-2.26 (m, 2H), 1.76-1.71 (m, 2H); MS (ES+) m/z 416.7 (M+1).

Sources & evidence

ORD record
ord-52b45bbfb2784f9ca02db8587c092b16
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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