Benzylamine → HCID 57744454, compound

HRID 1887261Notes

Reaction equation

[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[CH:12]=[CH:11][N:10]([C:13]3[S:14][C:15]([C:19]([OH:21])=O)=[C:16]([CH3:18])[N:17]=3)[C:9](=[O:22])[CH:8]=2)[CH2:3][CH2:2]1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([NH:30][C:19]([C:15]1[S:14][C:13]([N:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)=[CH:8][C:9]2=[O:22])=[N:17][C:16]=1[CH3:18])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 24986107HCID 24986107, compound

Product 1

HCID 57744454HCID 57744454, compoundYield 17%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 2-(4-(2-cyclopropylethoxy)-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 172-174° C. (hexane/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.64 (d, J=8.1 Hz, 1H), 7.37-7.26 (m, 5H), 6.16 (dd, J=8.1, 2.5 Hz, 1H), 6.09 (t, J=5.6 Hz, 1H), 5.97 (d, J=2.5 Hz, 1H), 4.58 (d, J=5.6 Hz, 2H), 4.03 (t, J=6.6 Hz, 2H), 2.68 (s, 3H), 1.68 (q, J=6.6 Hz, 2H), 0.89-0.72 (m, 1H), 0.52-0.46 (m, 2H), 0.13-0.08 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 167.8, 162.2, 162.1, 153.6, 152.1, 137.7, 131.3, 128.8, 127.9, 127.7, 122.2, 104.1, 96.6, 69.1, 44.1, 33.6, 17.3, 7.5, 4.2; MS (ES+) m/z 410.2 (M+1).

Sources & evidence

ORD record: ord-000df53a28b74d1a91da5a0641a96a89
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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