3-Fluoro-2-pyridinemethanamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-((3-fluoropyridin-2-yl)methyl)-4-methylthiazole-5-carboxamide

HRID 1882452Notes

Reaction equation

HRID 1882452 reaction equation
FC1C=C(CN)C=NC=1.[F:10][C:11]1[C:12]([CH2:17][NH2:18])=[N:13][CH:14]=[CH:15][CH:16]=1.[CH:19]1([CH2:22][N:23]2[CH2:27][CH2:26][N:25]([C:28]3[S:29][C:30]([C:34](O)=[O:35])=[C:31]([CH3:33])[N:32]=3)[C:24]2=[O:37])[CH2:21][CH2:20]1>>[CH:19]1([CH2:22][N:23]2[CH2:27][CH2:26][N:25]([C:28]3[S:29][C:30]([C:34]([NH:18][CH2:17][C:12]4[C:11]([F:10])=[CH:16][CH:15]=[CH:14][N:13]=4)=[O:35])=[C:31]([CH3:33])[N:32]=3)[C:24]2=[O:37])[CH2:20][CH2:21]1

Participants

4

Reactant 3

HCID 112057543-Fluoro-2-pyridinemethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579197872-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-((3-fluoropyridin-2-yl)methyl)-4-methylthiazole-5-carboxamideYield 60%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with (3-fluoropyridin-2-yl)methanamine to react with 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white solid in 60% yield: mp 142-144° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.38-8.31 (m, 2H), 7.69-7.62 (m, 1H), 7.39-7.33 (m, 1H), 4.51-4.54 (m, 2H), 4.00-3.95 (m, 2H), 3.64-3.59 (m, 2H), 3.06 (d, J=6.0 Hz, 2H), 2.44 (s, 3H), 0.96-0.87 (m, 1H), 0.49-0.42 (m, 2H), 0.21-0.16 (m, 2H); 13C NMR (75 MHZ, DMSO-d6) δ 162.2, 159.1, 157.9, 155.7, 151.2, 146.2, 145.4, 124.5, 123.6, 118.2, 48.2, 42.5, 42.3, 40.8, 17.5, 9.3, 3.6; MS (ES+) m/z 389.9 (M+1).

Sources & evidence

ORD record
ord-e8780b5adebf44178a0440cda63b0aaf
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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