5-Amino-4-(thiazol-2-yl)thiophene-3-carbonitrile → N-(4-cyano-3-(thiazol-2-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide
Reaction equation
[NH2:1][C:2]1[S:6][CH:5]=[C:4]([C:7]#[N:8])[C:3]=1[C:9]1[S:10][CH:11]=[CH:12][N:13]=1.[O:14]=[C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:21]=2)[N:16]1[CH2:29][C:30](O)=[O:31]>>[C:7]([C:4]1[C:3]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[C:2]([NH:1][C:30](=[O:31])[CH2:29][N:16]2[C:17]3[C:22](=[CH:21][C:20]([C:25]([F:26])([F:28])[F:27])=[CH:19][CH:18]=3)[CH:23]=[CH:24][C:15]2=[O:14])[S:6][CH:5]=1)#[N:8]Participants
Procedure
The title compound was prepared from 5-amino-4-(thiazol-2-yl)thiophene-3-carbonitrile (271 mg, 1 mmol) and 2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid (0.76 mmol) according to protocol A. The crude product was purified by column chromatography (35% EtOAc/hexanes) and HPLC to give N-(4-cyano-3-(thiazol-2-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide (24.mg) as a white solid with an m/z of 461.1 and retention of 7.348 min using the [7] LCMS method. 1H-NMR (300 MHz, CDCl3) δ 13.21 (s, 1H), 7.93 (m, 2H), 7.86 (dd, J=8.9, 1.8 Hz, 1H), 7.58 (s, 1H), 7.54 (d, J=3.4 Hz, 1H), 7.46 (d, J=8.8 Hz, 1H), 7.31 (d, J=3.3 Hz, 1H), 7.00 (d, J=9.6 Hz, 1H), 5.35 (s, 2H). 13C-NMR (75 MHz, CDCl3) δ 165.3, 161.7, 161.0, 140.8, 140.0, 139.9, 129.4, 128.0, 126.5, 122.7, 120.4, 117.8, 115.9, 115.0, 114.7, 106.0, 46.3.
Workup
- customThe crude product was purified by column chromatography (35% EtOAc/hexanes) and HPLC
Sources & evidence
- ORD record
- ord-4730c479fef14871bb0238f2566518b5
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450363B2
Reaction notes
Loading…