4-bromo-3-(2H-1,2,3-triazol-2-yl)thiophene-2-amine → N-(4-Bromo-3-(2H-1,2,3-triazol-2-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide

HRID 1519868Notes

Reaction equation

HRID 1519868 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=2)[N:3]1[CH2:16][C:17]([OH:19])=O.[Br:20][C:21]1[C:22]([N:27]2[N:31]=[CH:30][CH:29]=[N:28]2)=[C:23]([NH2:26])[S:24][CH:25]=1>>[Br:20][C:21]1[C:22]([N:27]2[N:31]=[CH:30][CH:29]=[N:28]2)=[C:23]([NH:26][C:17](=[O:19])[CH2:16][N:3]2[C:4]3[C:9](=[CH:8][C:7]([C:12]([F:13])([F:14])[F:15])=[CH:6][CH:5]=3)[CH:10]=[CH:11][C:2]2=[O:1])[S:24][CH:25]=1

Participants

3

Reactant 2

HCID 687570274-bromo-3-(2H-1,2,3-triazol-2-yl)thiophene-2-amineHCID 687598572-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid

Product 1

HCID 46869354N-(4-Bromo-3-(2H-1,2,3-triazol-2-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide

Procedure

The title compound was prepared from 2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid (0.31 g, 1.14 mmol) and 4-bromo-3-(2H-1,2,3-triazol-2-yl)thiophene-2-amine (0.35 g, 1.42 mmol) according to protocol A. The desired product was submitted to prep HPLC for further purification. Retention time (min)=6.9, method [7], MS(ESI) 498.0 (M+H). 1H NMR (CDCl3) δ 10.56 (s, 1H), 7.90-7.89 (m, 2H), 7.86 (s, 1H), 7.83 (d, J=8.9 Hz, 1H), 7.66 (d, J=8.9 Hz, 1H), 6.97 (s, 1H), 6.92 (d, J=8.9 Hz, 2H), 5.16 (s, 2H).

Workup

  1. customfor further purification

Sources & evidence

ORD record
ord-192a6dd3a8094f498e5a29df4d300f31
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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