2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid → N-(4-Cyano-3-(1H-1,2,3-triazol-1-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide

HRID 2098077Notes

Reaction equation

HRID 2098077 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.[NH2:20][C:21]1[S:25][CH:24]=[C:23]([C:26]#[N:27])[C:22]=1[N:28]1[CH:32]=[CH:31][N:30]=[N:29]1>>[C:26]([C:23]1[C:22]([N:28]2[CH:32]=[CH:31][N:30]=[N:29]2)=[C:21]([NH:20][C:17](=[O:19])[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 687869335-amino-4-(1H-1,2,3-triazol-1-yl)thiophene-3-carbonitrile

Product 1

HCID 59636652N-(4-Cyano-3-(1H-1,2,3-triazol-1-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 (0.072 g, 0.27 mmol) and 5-amino-4-(1H-1,2,3-triazol-1-yl)thiophene-3-carbonitrile (0.025 g, 0.13 mmol) according to protocol A. The crude product was purified by prep HPLC. LCMS retention time (min)=5.505, method [7], MS (ESI) 445.1 (M+H). 1H NMR (CDCl3) δ 11.17 (s, 1H), 8.41 (s, 1H), 7.91-7.87 (m, 3H), 7.79 (d, J=9.0 Hz, 1H), 7.67 (s, 1H), 7.48 (d, J=9.0 Hz, 1H), 5.26 (s, 2H).

Workup

  1. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-973627a667a443c688157e05594c12d7
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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