4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine → N-(4-Bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(2-oxo-7-(trifluoromethoxy)quinolin-1(2H)-yl)acetamide

HRID 2098010Notes

Reaction equation

HRID 2098010 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:7][CH:8]=2)[N:3]1[CH2:17][C:18]([OH:20])=O.[Br:21][C:22]1[C:23]([C:28]2[NH:32][N:31]=[CH:30][N:29]=2)=[C:24]([NH2:27])[S:25][CH:26]=1>>[Br:21][C:22]1[C:23]([C:28]2[NH:32][N:31]=[CH:30][N:29]=2)=[C:24]([NH:27][C:18](=[O:20])[CH2:17][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[C:6]([O:12][C:13]([F:16])([F:15])[F:14])[CH:5]=3)[CH:10]=[CH:11][C:2]2=[O:1])[S:25][CH:26]=1

Participants

3

Reactant 2

HCID 596366864-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amineHCID 687849432-(2-oxo-7-(trifluoromethoxy)quinolin-1(2H)-yl)acetic acid

Product 1

HCID 56668697N-(4-Bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(2-oxo-7-(trifluoromethoxy)quinolin-1(2H)-yl)acetamide

Procedure

The title compound was prepared from 2-(2-oxo-7-(trifluoromethoxy)quinolin-1(2H)-yl)acetic acid (79 mg, 0.275 mmol) and 4-bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-amine (35 mg, 0.137 mmol) according to protocol A. Retention time (min)=6.037, method [7], MS (ESI) 514.0 (M+H); 1H NMR (300 MHz, CD3OD) δ 8.15 (s, 1H), 8.11 (d, J=9.9 Hz, 1H), 7.88 (d, J=9.1 Hz, 1H), 7.41 (s, 1H), 7.26 (m, 1H), 7.10 (s, 1H), 6.81 (d, J=9.9 Hz, 1H), 5.31 (s, 2H).

Sources & evidence

ORD record
ord-40c9d54a84aa4461b9807427f26da0b2
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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