5-Amino-4-(thiazol-2-yl)thiophene-3-carbonitrile → N-(4-cyano-3-(thiazol-2-yl)thiophen-2-yl)-2-(2-oxo-3,4-dihydro-1,5-naphthyridin-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[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][N:21]=2)[N:16]1[CH2:25][C:26](O)=[O:27]>>[C:7]([C:4]1[C:3]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[C:2]([NH:1][C:26](=[O:27])[CH2:25][N:16]2[C:17]3[C:22](=[N:21][CH:20]=[CH:19][CH:18]=3)[CH2:23][CH2:24][C:15]2=[O:14])[S:6][CH:5]=1)#[N:8]Participants
3
Procedure
The title compound was prepared from 5-amino-4-(thiazol-2-yl)thiophene-3-carbonitrile (67 mg, 0.32 mmol) and 2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetic acid (100 mg, 0.48 mmol) according to protocol A. The crude product was purified by column chromatography (2% methanol/methylene chloride) and HPLC to give N-(4-cyano-3-(thiazol-2-yl)thiophen-2-yl)-2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetamide (5.4 mg) as a white solid. LCMS m/z 396.1, method [7] retention time 2.611 min. 1H-NMR (300 MHz, CDCl3) δ 8.39 (d, J=4.1 Hz, 1H), 7.76 (d, J=3.3 Hz, 2H), 7.62 (s, 1H), 7.58 (d, J=7.4 Hz, 1H), 7.44 (m, 2H), 3.46 (t, J=7.1 Hz, 2H), 3.02 (t, J=7.2 Hz, 2H).