3-Pyridinemethanamine → HCID 178426591, compound

HRID 554952Notes

Reaction equation

HRID 554952 reaction equation
N1C=CC=C(CN)C=1.[CH3:9][C:10]1[CH:14]=[C:13]([CH2:15][NH2:16])[NH:12][N:11]=1.[F:17][C:18]1[CH:39]=[CH:38][C:21]([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])=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[CH2:27][CH2:26][N:25]([C:28]3[S:29][C:30]([C:34]([NH:16][CH2:15][C:13]4[NH:12][N:11]=[C:10]([CH3:9])[CH:14]=4)=[O:35])=[C:31]([CH3:33])[N:32]=3)[C:24]2=[O:37])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579197992-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 178426643HCID 178426643, compound

Product 1

HCID 178426591HCID 178426591, compound

Procedure

Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with (3-methyl-1H-pyrazol-5-yl)methanamine to react 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid instead of (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as an off-white solid (0.04 g, 12%): mp 225-226° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.30 (t, J=5.0 Hz, 1H), 7.38-7.34 (m, 2H), 7.23-7.17 (m, 2H), 5.89 (s, 1H), 4.42 (s, 2H), 4.29 (d, J=5.7 Hz, 2H), 4.02-3.97 (m, 2H), 2.48-3.42 (m, 2H), 2.46 (s, 3H), 2.16 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.6, 161.5 (d, 1JC-F=243 Hz), 157.3, 155.0, 150.5 (br), 132.6 (d, 4JC-F=3 Hz), 129.9 (d, 3JC-F=8 Hz), 118.2, 115.4 (d, 2JC-F=21 Hz), 102.5, 46.1, 41.9, 41.5, 36.8 (br), 17.0, 10.6 (br); MS (ES+) m/z 428.9 (M+1).

Sources & evidence

ORD record
ord-34c0c0fd9f7e4544beb363a9bfe0b5c8
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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