3-Fluorobenzylamine → HCID 54742333, compound

HRID 1887272Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[S:9][C:10]([C:14]([OH:16])=O)=[C:11]([CH3:13])[N:12]=2)[C:4](=[O:17])[CH:3]=1.[F:18][C:19]1[CH:20]=[C:21]([CH2:25][NH2:26])[CH:22]=[CH:23][CH:24]=1>>[F:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[CH2:25][NH:26][C:14]([C:10]1[S:9][C:8]([N:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][C:4]2=[O:17])=[N:12][C:11]=1[CH3:13])=[O:16]

Participants

Reactant 2

HCID 668533-Fluorobenzylamine

HCID 547423412-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 54742333HCID 54742333, compoundYield 44%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 2-(4-hydroxy-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 (3-fluorophenyl)methanamine, the title compound was obtained as a colorless solid in 44% yield: mp 250-252° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 11.50 (br s, 1H), 8.78 (t, J=6.0 Hz, 1H), 8.59 (d, J=8.0 Hz, 1H), 7.39-7.30 (m, 1H), 7.13-7.00 (m, 3H), 6.26 (dd, J=8.0, 2.5 Hz, 1H), 5.82 (d, J=2.5 Hz, 1H), 4.39 (d, J=5.9 Hz, 2H), 2.53 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.9, 164.2, 162.1, 161.6, 154.2, 142.9, 142.8, 132.6, 130.7, 123.7, 123.4, 114.5, 114.1, 104.4, 98.0, 42.6, 17.5; MS (ES+) m/z: 360.2 (M+1).

Sources & evidence

ORD record: ord-496b3d7636684cc0b92275f398d85dc5
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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