5-Amino-4-(thiazol-5-yl)thiophene-3-carbonitrile → N-(4-Cyano-3-(thiazol-5-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide

HRID 2098144Notes

Reaction equation

HRID 2098144 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[C:28]1[S:32][CH:31]=[N:30][CH:29]=1>>[C:26]([C:23]1[C:22]([C:28]2[S:32][CH:31]=[N:30][CH: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:13])([F:14])[F:15])=[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 687545995-Amino-4-(thiazol-5-yl)thiophene-3-carbonitrileHCID 687598572-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid

Product 1

HCID 59636675N-(4-Cyano-3-(thiazol-5-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 (0.047 g, 0.17 mmol) and 5-amino-4-(thiazol-5-yl)thiophene-3-carbonitrile (0.055, 0.26 mmol) according to protocol A. The crude product was purified by prep HPLC. Retention time (min)=5.989, method [7], MS (ESI) 461.1 (M+H). 1H NMR (CDCl3) δ 9.95 (s, 1H), 7.91-7.85 (m, 4H) 7.78 (d, J=8.7 Hz, 1H), 7.63 (s, 1H), 6.84 (d, J=8.7 Hz, 1H), 5.06 (s, 2H).

Workup

  1. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-342d8d0722694528811bca736ff75e8a
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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