Benzylamine → HCID 178433080, compound

HRID 1887265Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[NH:16][C:17]([C:21]([OH:23])=O)=[C:18]([CH3:20])[N:19]=2)[C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([NH:32][C:21]([C:17]1[NH:16][C:15]([N:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][C:11]2=[O:24])=[N:19][C:18]=1[CH3:20])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 178433082HCID 178433082, compound

Product 1

HCID 178433080HCID 178433080, compoundYield 59%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-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 59% yield: mp 183-184° C.; 1H NMR (300 MHz, CDCl3) δ 11.86 (br s, 1H), 8.42 (d, J=8.0 Hz, 1H), 7.43-7.26 (m, 10H), 6.18 (dd, J=8.0, 2.6 Hz, 1H), 6.04 (d, J=2.6 Hz, 1H), 5.05 (s, 2H), 4.61 (d, J=6.0 Hz, 2H), 2.65 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 167.4, 163.6, 163.4, 138.8, 134.6, 132.2, 129.5, 128.8, 128.7, 128.6, 127.8, 127.8, 127.3, 126.9, 103.5, 98.4, 70.7, 42.7, 11.0; MS (ES+) m/z 415.2 (M+1).

Sources & evidence

ORD record: ord-1e23d0cdd7a849ca8265dbc32a7cf8a2
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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