2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid → HCID 178521249, compound

HRID 2098046Notes

Reaction equation

HRID 2098046 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[C:4]([NH2:7])[S:5][CH:6]=1.[O:13]=[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:20]=2)[N:15]1[CH2:28][C:29](O)=[O:30]>>[Cl:1][C:2]1[C:3]([C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[C:4]([NH:7][C:29](=[O:30])[CH2:28][N:15]2[C:16]3[C:21](=[CH:20][C:19]([C:24]([F:25])([F:27])[F:26])=[CH:18][CH:17]=3)[CH:22]=[CH:23][C:14]2=[O:13])[S:5][CH:6]=1

Participants

3

Reactant 2

HCID 687598572-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acidHCID 178509326HCID 178509326, compound

Product 1

HCID 178521249HCID 178521249, compoundYield 55%

Procedure

The title compound was prepared from 4-chloro-3-(1H-1,2,4-triazol-3-yl)thiophen-2-amine (502 mg, 2.50 mmol) and 2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid (675 mg, 2.49 mmol) using protocol A (626 mg, 55% yield). Method [7] Retention time 5.59 min by HPLC (M+=454 and 456) and (M+Na=476 and 478). 1H NMR (300 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.38 (broad s, 1H), 8.27 (s, 1H), 8.22 (d, J=9.3 Hz, 1H), 7.89 (d, J=9.3 Hz, 1H), 7.70 (d, J=9.3, 1H), 7.17 (s, 1H), 6.87 (d, J=9.9 Hz, 1H), 5.31 (s, 2H).

Sources & evidence

ORD record
ord-f1afa4abd19e435ea7ffeb259dde4195
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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