3-Pyridinemethanamine → HCID 24984278, compound

HRID 1887269Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]([C:9]2[S:10][C:11]([C:15]([OH:17])=O)=[C:12]([CH3:14])[N:13]=2)[C:5](=[O:18])[CH:4]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH2:26])[CH:20]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]([C:9]2[S:10][C:11]([C:15]([NH:26][CH2:25][C:21]3[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=3)=[O:17])=[C:12]([CH3:14])[N:13]=2)[C:5](=[O:18])[CH:4]=1

Participants

Reactant 2

HCID 310183-Pyridinemethanamine

HCID 57744478HCID 57744478, compound

Product 1

HCID 24984278HCID 24984278, compoundYield 58%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 2-(4-methoxy-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 58% yield: mp 200-202° C. (dichloromethane/methanol); 1H NMR (300 MHz, CDCl3) δ 8.64 (d, J=8.1 Hz, 1H), 8.60-8.59 (m, 1H), 8.52-8.51 (m, 1H), 7.51-7.68 (m, 1H), 7.29-7.24 (m, 1H), 6.30 (t, J=5.8 Hz, 1H), 6.17 (dd, J=8.1, 2.6 Hz, 1H), 5.96 (d, J=2.6 Hz, 1H), 4.61 (d, J=5.8 Hz, 2H), 3.82 (s, 3H), 2.67 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 168.4, 162.4, 162.1, 153.6, 152.6, 149.2, 149.0, 135.7, 133.7, 131.4, 123.6, 121.8, 103.9, 96.2, 56.0, 41.4, 17.3; MS (ES+) m/z 357.2 (M+1).

Sources & evidence

ORD record: ord-e10dc920c8414c9ca32c04f921688585
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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