Benzylamine → HCID 24985101, compound

HRID 1887260Notes

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

Participants

Reactant 2

HCID 7504Benzylamine

HCID 57744478HCID 57744478, compound

Product 1

HCID 24985101HCID 24985101, compoundYield 17%

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 benzylamine, the title compound was obtained as a colorless solid in 17% yield: mp 205-208° C. (hexane/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 8.78 (t, J=6.0 Hz, 1H), 8.59 (d, J=8.1 Hz, 1H), 7.35-7.17 (m, 5H), 6.33 (dd, J=8.1, 2.7 Hz, 1H), 6.11 (d, J=2.7 Hz, 1H), 4.38 (d, J=6.0 Hz, 2H), 3.81 (s, 3H), 2.54 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 168.6, 161.9, 161.6, 153.9, 150.3, 139.9, 132.0, 128.7, 127.2, 123.7, 104.2, 86.5, 56.8, 43.1, 17.5; MS (ES+) m/z 356.2 (M+1).

Sources & evidence

ORD record: ord-d2d3f9dee27d4549b573bde874ae7169
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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