2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid → HCID 59636656, compound

HRID 2098078Notes

Reaction equation

HRID 2098078 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](O)=[O:18].[NH2:20][C:21]1[S:25][CH:24]=[C:23]([C:26]#[N:27])[C:22]=1[N:28]1[N:32]=[CH:31][CH:30]=[N:29]1>>[C:26]([C:23]1[C:22]([N:28]2[N:32]=[CH:31][CH:30]=[N:29]2)=[C:21]([NH:20][C:17](=[O:18])[CH2:16][N:3]2[C:4]3[C:9](=[CH:8][C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][CH:5]=3)[CH:10]=[CH:11][C:2]2=[O:1])[S:25][CH:24]=1)#[N:27]

Participants

3

Reactant 2

HCID 687598572-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acidHCID 68784543HCID 68784543, compound

Product 1

HCID 59636656HCID 59636656, compound

Procedure

N-(4-cyano-3-(2H-1,2,3-triazol-2-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide was prepared from 2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid (0.15 g, 0.56 mmol) and 5-amino-4-(2H-1,2,3-triazol-2-yl)thiophene-3-carbonitrile (0.070 g, 0.37 mmol) according to protocol A. The crude product was purified by prep HPLC. Retention time (min)=6.5, method [7], MS (ESI) 467.1 (M+Na). 1H NMR (CDCl3) δ 11.50 (s, 1H), 7.93-7.85 (m, 4H), 7.83 (s, 1H), 7.64 (s, 1H), 7.60 (d, J=8.5 Hz, 1H), 6.95 (d, J=9.7 Hz, 1H), 5.29 (s, 2H).

Workup

  1. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-b00f7f4113b947a985c6afcbe10d4baa
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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