Benzylamine → HCID 24985789, compound

HRID 1887267Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[N:16]([CH3:24])[C:17]([C:21](O)=[O:22])=[C:18]([CH3:20])[N:19]=2)[C:11](=[O:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([NH:33][C:21]([C:17]1[N:16]([CH3:24])[C:15]([N:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]2=[O:25])=[N:19][C:18]=1[CH3:20])=[O:22])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 24986114HCID 24986114, compound

Product 1

HCID 24985789HCID 24985789, compoundYield 62%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-1,4-dimethyl-1H-imidazole-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 62% yield: mp 232-233° C.; 1H NMR (300 MHz, CDCl3) δ 7.43-7.29 (m, 10H), 7.19 (d, J=7.7 Hz, 1H), 6.17 (t, J=5.6 Hz, 1H), 6.09 (dd, J=7.7, 2.5 Hz, 1H), 5.96 (d, J=2.5 Hz, 1H), 5.02 (s, 2H), 4.62 (d, J=5.6 Hz, 2H), 3.67 (s, 3H), 2.39 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 168.3, 163.3, 160.9, 141.5, 138.0, 137.8, 136.8, 134.7, 128.84, 128.8, 128.6, 127.7, 127.7, 127.6, 123.5, 102.8, 97.8, 70.6, 43.6, 32.7, 15.2; MS (ES+) m/z 429.3 (M+1).

Sources & evidence

ORD record: ord-12b95917ce3b4b728e68f43fb62980c2
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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