Cesium carbonate → N-[3-(Dimethylamino)propyl]-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][CH2:17][N:18]([CH3:20])[CH3:19])[CH3:14])=[O:12])[S:10][C:3]=12.[OH:21][C:22]1[CH:30]=[C:29]2[C:25]([C:26]([C:33]([NH:35][CH3:36])=[O:34])=[C:27]([CH3:32])[N:28]2[CH3:31])=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:19][N:18]([CH3:20])[CH2:17][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:21][C:22]2[CH:30]=[C:29]3[C:25]([C:26]([C:33]([NH:35][CH3:36])=[O:34])=[C:27]([CH3:32])[N:28]3[CH3:31])=[CH:24][CH:23]=2)[CH:8]=1)=[O:12]Participants
4
Reactant 3
Product 1
Procedure
This material was prepared by the reaction of 7-chloro-N-[3-(dimethylamino)propyl]-N-methylthieno[3,2-b]pyridine-2-carboxamide 32a (0.095 g, 0.32 mmole) with 6-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamide (0.070 g, 0.32 mmole) 16e and Cs2CO3 (0.104 g, 0.32 mmole) in a manner as described previously for example 1 to give a white solid (0.098 g, 62%). 1H NMR (300 MHz, CD3OD) δ8.53 (1H, d, J=5.3 Hz), 7.91 (2H, m), 7.38 (1H, s), 7.09 (1H, dd, J=2.1, 8.7 Hz), 6.81 (1H, d, J=5.3 Hz), 3.73 (3H, s), 3.66 (2H, m), 3.28 (2H, m), 3.01 (3H, s), 2.68 (9H, m), 2.06 (2H, m), 1.94 (3H, s); HRMS (MH+): Calcd: 494.2223; Found: 494.2226.
Sources & evidence
- ORD record
- ord-62df86e59bee41359a46fbbc4580fdab
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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