3-Pyridinemethanamine → HCID 178433081, compound

HRID 1887266Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[NH:16][C:17]([C:21](O)=[O:22])=[C:18]([CH3:20])[N:19]=2)[C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[NH:16][C:17]([C:21]([NH:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:22])=[C:18]([CH3:20])[N:19]=2)[C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 310183-Pyridinemethanamine

HCID 178433082HCID 178433082, compound

Product 1

HCID 178433081HCID 178433081, compoundYield 63%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-1H-imidazole-5-carboxylic acid in place of 4-methyl-2-(2-oxo-4-phenylpyridin-1(2H)-yl)thiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 63% yield: mp 203-204° C.; 1H NMR (300 MHz, DMSO-d6) δ 12.70 (br s, 1H), 8.58-8.51 (m, 2H), 8.43 (d, J=3.9 Hz, 1H), 8.01 (d, J=7.8 Hz, 1H), 7.70 (d, J=7.8 Hz, 1H), 7.50-7.29 (m, 6H), 6.23 (dd, J=7.8, 2.6 Hz, 1H), 6.07 (d, J=2.6 Hz, 1H), 5.16 (s, 2H), 4.40 (d, J=6.3 Hz, 2H), 2.47 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.2, 162.9, 162.0, 148.8, 147.8, 137.3, 135.9, 135.6, 135.4, 135.1, 130.8, 128.5, 128.2, 128.0, 127.4, 123.3, 101.6, 97.5, 70.0, 10.5; MS (ES+) m/z 416.3 (M+1).

Sources & evidence

ORD record: ord-b97e3cb3f5064eac93346f262f3409ee
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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