3-Pyridinemethanamine → HCID 178426592, compound

HRID 1882425Notes

Reaction equation

HRID 1882425 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[C:27](=[O:28])[N:26]([C:29]3[S:30][C:31]([C:35](O)=[O:36])=[C:32]([CH3:34])[N:33]=3)[CH:25]=[N:24]2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[C:27](=[O:28])[N:26]([C:29]3[S:30][C:31]([C:35]([NH:16][CH2:15][C:13]4[NH:12][N:11]=[C:10]([CH3:9])[CH:14]=4)=[O:36])=[C:32]([CH3:34])[N:33]=3)[CH:25]=[N:24]2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579198022-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acidHCID 178426643HCID 178426643, compound

Product 1

HCID 178426592HCID 178426592, compoundYield 31%

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 with 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-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 in 31% yield: mp 234-235° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.76 (s, 1H), 8.67 (t, J=5.5 Hz, 1H), 7.41-7.36 (m, 2H), 7.27-7.16 (m, 2H), 5.91 (s, 1H), 5.00 (s, 2H), 4.37-4.31 (m, 2H), 2.55 (s, 3H), 2.19-2.12 (m, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.7 (d, 1JC-F=244 Hz), 160.7, 151.2, 150.5, 149.7, 149.6, 138.7, 132.2 (d, 4JC-F=3 Hz), 132.1, 130.0 (d, 3JC-F=8 Hz), 122.9, 115.4 (d, 2JC-F=22 Hz), 102.3, 47.7, 37.3, 16.9, 10.4; MS (ES+) m/z 427.8 (M+1), MS (ES−) m/z 425.8 (M−1).

Sources & evidence

ORD record
ord-9445efb91b7d4ee79509bde0f2b49ec0
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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