2-(3-Trifluoromethylquinolin-5-yl)acetic acid hydrogen chloride → N-(4-bromo-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(3-(trifluoromethyl)quinolin-5-yl)acetamide

HRID 1519825Notes

Reaction equation

HRID 1519825 reaction equation
[Br:1][C:2]1[C:3]([C:8]2[NH:12][CH:11]=[N:10][N:9]=2)=[C:4]([NH2:7])[S:5][CH:6]=1.Cl.[F:14][C:15]([F:31])([F:30])[C:16]1[CH:17]=[N:18][C:19]2[C:24]([CH:25]=1)=[C:23]([CH2:26][C:27](O)=[O:28])[CH:22]=[CH:21][CH:20]=2>>[Br:1][C:2]1[C:3]([C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[C:4]([NH:7][C:27](=[O:28])[CH2:26][C:23]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:24]=2[CH:25]=[C:16]([C:15]([F:14])([F:31])[F:30])[CH:17]=[N:18]3)[S:5][CH:6]=1

Participants

3

Reactant 2

HCID 687571072-(3-Trifluoromethylquinolin-5-yl)acetic acid hydrogen chlorideHCID 178509325HCID 178509325, compound

Product 1

HCID 178520202N-(4-bromo-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(3-(trifluoromethyl)quinolin-5-yl)acetamide

Procedure

The title compound was prepared from 4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine (56 mg, 228 umol) and 2-(3-trifluoromethylquinolin-5-yl)acetic acid hydrogen chloride (200 mg, 784 umol) according to the procedures outlined in Example 1.68.6., above. Method [7] retention time 5.93 min by HPLC (M+ 482 and 484) and (M+Na 504 and 506). 1H NMR (300 MHz, CDCl3) δ 12.45 (s, 1H), 9.23 (s, 1H), 8.84 (s, 1H), 8.37 (d, J=8.4 Hz, 1H), 8.03 (m, 1H), 7.85 (d, J=6.9 Hz, 1H), 7.74 (s, 1H), 6.95 (s, 1H), 4.38 (s, 2H).

Sources & evidence

ORD record
ord-9fe8d55dd3d445a99743a21d6f6fab78
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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