Benzylamine → HCID 24985100, compound

HRID 1887259Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][N:9]([C:12]3[S:13][C:14]([C:18]([OH:20])=O)=[C:15]([CH3:17])[N:16]=3)[C:8](=[O:21])[CH:7]=2)[CH2:3][CH2:2]1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([NH:29][C:18]([C:14]1[S:13][C:12]([N:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)=[CH:7][C:8]2=[O:21])=[N:16][C:15]=1[CH3:17])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 24985953HCID 24985953, compound

Product 1

HCID 24985100HCID 24985100, compoundYield 58%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 2-(4-(cyclopropylmethoxy)-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 white solid in 58% yield: mp 218-220° C. (hexane/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 8.77 (t, J=5.9 Hz, 1H), 8.58 (d, J=8.1 Hz, 1H), 7.35-7.18 (m, 5H), 6.34 (dd, J=8.1, 2.7 Hz, 1H), 6.05 (d, J=2.7 Hz, 1H), 4.38 (d, J=5.9 Hz, 2H), 3.88 (d, J=7.2 Hz, 2H), 2.53 (s, 3H), 1.26-1.10 (m, 1H), 0.52-0.50 (m, 2H), 0.32-0.27 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 167.8, 161.9, 161.6, 153.8, 150.3, 139.9, 131.9, 128.7, 127.7, 127.2, 123.6, 104.4, 96.8, 73.9, 43.1, 17.5, 9.9, 3.6; MS (ES+) m/z 396.2 (M+1).

Sources & evidence

ORD record: ord-54e70fc48b034005992167781e6ac44c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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