Cesium carbonate → HCID 69328078, compound

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[NH:10][C:9]2[CH:13]=[CH:14][S:15][C:8]=2[C:7]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[O:23])[CH2:18][CH2:17]1)=[O:5])[CH3:2].[C:29]([O-])([O-])=O.[Cs+].[Cs+].Cl.ClC[C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1>CN1C(=O)CCC1>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]([C:38]2[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=2)[C:9]2[CH:13]=[C:14]([CH3:29])[S:15][C:8]=2[C:7]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[O:23])[CH2:18][CH2:17]1)=[O:5])[CH3:2]

Participants

Procedure

A solution of 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (5) (856 mg, 2.05 mmol), Cs2CO3 (2.75 g, 8.4 mmol), 3-chloromethyl pyridine hydrochloride (0.370 g, 2.25 mmol) and KI (1 g) in dry NMP was heated overnight at 90° C. The solution was poured into ice water and the solids formed were filtered, washed by cold water, and dried. The crude product was purified by reverse phase flash chromatography in combiflash eluting with water/acetonitrile gradient. 1H-NMR (DMSO-d6) δ 3.13 (t, J=7.2 Hz, 3H), 3.80 (m, 4H), 4.27 (q, J=7.2 Hz, 2H), 5.40 (s, 2H), 7.15 (m, 1H), 7.35 (m, 1H), 7.44 (d, J=6.0 Hz, 1H), 7.48 (dd, J=1.2, 3.6 Hz, 1H), 7.60 (m, 1H), 7.79 (dd, J=0.8, 4.8 Hz, 1H), 8.06 (d, J=5.6 Hz, 1H), 8.47 (dd, J=1.6, 4.8 Hz, 1H), 8.56 (d, J=1.6 Hz, 1H); EIMS m/z 509 (M+1).