4-Fluorobenzylamine → HCID 24983858, compound

HRID 1887271Notes

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.[F:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH2:34])=[CH:29][CH:28]=1>>[F:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:20]([C:16]2[S:15][C:14]([N:11]3[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:25][CH:24]=4)=[CH:9][C:10]3=[O:23])=[N:18][C:17]=2[CH3:19])=[O:22])=[CH:29][CH:28]=1

Participants

Reactant 2

HCID 673264-Fluorobenzylamine

HCID 57744499HCID 57744499, compound

Product 1

HCID 24983858HCID 24983858, compoundYield 34%

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 (4-fluorophenyl)methanamine, the title compound was obtained as a colorless solid in 34% yield: mp 249-251° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 8.78 (t, J=5.9 Hz, 1H), 8.60 (d, J=8.1 Hz, 1H), 7.51-7.47 (m, 2H), 7.34-7.29 (m, 2H), 7.25-7.08 (m, 4H), 6.37 (dd, J=8.1, 2.7 Hz, 1H), 6.23 (d, J=2.7 Hz, 1H), 5.14 (s, 2H), 4.35 (d, J=5.9 Hz, 2H), 2.53 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.4, 164.1, 163.2, 161.9, 160.9, 153.9, 150.4, 136.1, 132.1, 131.0, 130.9, 129.8, 123.6, 116.0, 115.7, 104.3, 97.5, 70.1, 42.4, 17.5; MS (ES+) m/z 468.3 (M+1).

Sources & evidence

ORD record: ord-04b18bb0dbcb4d67bf56f5ceebb53047
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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