3-Pyridinemethanamine → HCID 24984280, compound

HRID 1887270Notes

Reaction equation

[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[S:15][C:16]([C:20]([OH:22])=O)=[C:17]([CH3:19])[N:18]=3)[C:10](=[O:23])[CH:9]=2)=[CH:4][CH:3]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][NH2:33])[CH:27]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[S:15][C:16]([C:20]([NH:33][CH2:32][C:28]4[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=4)=[O:22])=[C:17]([CH3:19])[N:18]=3)[C:10](=[O:23])[CH:9]=2)=[CH:24][CH:25]=1

Participants

Reactant 2

HCID 310183-Pyridinemethanamine

HCID 57744499HCID 57744499, compound

Product 1

HCID 24984280HCID 24984280, compoundYield 52%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 2-(4-(4-fluorobenzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid in place of 4-methyl-2-(2-oxo-4-phenylpyridin-1(2H)-yl)thiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a colorless solid in 52% yield: mp 231-233° C. (dichloromethane/methanol); 1H NMR (300 MHz, DMSO-d6) δ 8.83 (t, J=5.6 Hz, 1H), 8.60 (d, J=8.1 Hz, 1H), 8.50 (s, 1H), 8.43 (d, J=4.2 Hz, 1H), 7.69 (d, J=7.9 Hz, 1H), 7.51-7.47 (m, 2H), 7.37-7.29 (m, 1H), 7.22 (t, J=8.8 Hz, 2H), 6.41-6.35 (m, 1H), 6.23 (s, 1H), 5.13 (s, 2H) 4.40 (d, J=4.2 Hz, 2H), 2.53 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.4, 164.1, 162.0, 161.6, 160.9, 154.0, 150.6, 149.3, 148.5, 135.6, 132.1, 131.0, 130.9, 123.9, 116.0, 115.7, 104.4, 97.5, 70.1, 42.2, 17.5; MS (ES+) m/z 451.3 (M+1).

Sources & evidence

ORD record: ord-26bf9832d30d4ae2aaf3fb4a2554e935
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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