Cesium carbonate → N-[2-(Dimethylamino)ethyl]-7-({1,2-dimethyl-3-[(methylamino)carbonyl]-1H-indol-6-yl}oxy)-N-methylthieno[3,2-b]pyridine-2-carboxamide
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH3:14])=[O:12])[S:10][C:3]=12.[CH3:20][NH:21][C:22]([C:24]1[C:32]2[C:27](=[CH:28][C:29]([OH:33])=[CH:30][CH:31]=2)[N:26]([CH3:34])[C:25]=1[CH3:35])=[O:23].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:18][N:17]([CH3:19])[CH2:16][CH2:15][N:13]([CH3:14])[C:11]([C:9]1[S:10][C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[O:33][C:29]2[CH:28]=[C:27]3[C:32]([C:24]([C:22]([NH:21][CH3:20])=[O:23])=[C:25]([CH3:35])[N:26]3[CH3:34])=[CH:31][CH:30]=2)[CH:8]=1)=[O:12]Participants
4
Reactant 3
Product 1
Procedure
This material was prepared by the reaction of 7-chloro-N-[2-(dimethylamino)ethyl]-N-methylthieno[3,2-b]pyridine-2-carboxamide 29a (0.167 g, 0.56 mmole) with 6-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamide 16e (0.123 g, 0.56 mmole) and Cs2CO3 (0.182 g, 0.56 mmole) in a manner as previously described for example 1 to give a yellow solid (0.040 g, 13%). 1H NMR (400 MHz, CD3OD) δ 8.71 (1H, d, J=6.8 Hz), 8.06 (1H, s), 7.83 (1H, d, J=8.6 Hz), 7.46 (1H, d, J=2.0 Hz), 7.09 (1H, d, J=6.8 Hz), 7.05 (1H, dd, J=2.0, 8.6 Hz), 3.90 (2H, t, J=5.8 Hz), 3.64 (3H, s), 3.42 (2H, t, J=5.8 Hz), 3.23 (6H, s), 2.93 (3H, s), 2.88 (3H, s), 2.58 (3H, s). HRMS (MH+): Calcd: 480.2090. Found: 480.2069.
Sources & evidence
- ORD record
- ord-a958433290b445c1952c95a934582c12
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07045528B2
Reaction notes
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