Cesium carbonate → 6-[(2-{[(3R)-3-(Dimethylamino)pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-N,1,2-trimethyl-1H-indole-3-carboxamide

HRID 985221Notes

Reaction equation

HRID 985221 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][C@@H:15]([N:18]([CH3:20])[CH3:19])[CH2:14]3)=[O:12])[S:10][C:3]=12.[CH3:21][NH:22][C:23]([C:25]1[C:33]2[C:28](=[CH:29][C:30]([OH:34])=[CH:31][CH:32]=2)[N:27]([CH3:35])[C:26]=1[CH3:36])=[O:24].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:19][N:18]([CH3:20])[C@@H:15]1[CH2:16][CH2:17][N:13]([C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[O:34][C:30]3[CH:29]=[C:28]4[C:33]([C:25]([C:23]([NH:22][CH3:21])=[O:24])=[C:26]([CH3:36])[N:27]4[CH3:35])=[CH:32][CH:31]=3)[CH:8]=2)=[O:12])[CH2:14]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 20745989(R)-(7-Chlorothieno[3,2-b]pyridin-2-yl)(3-(dimethylamino)pyrrolidin-1-yl)methanoneHCID 221435306-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamide

Product 1

HCID 599907866-[(2-{[(3R)-3-(Dimethylamino)pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-N,1,2-trimethyl-1H-indole-3-carboxamideYield 40.8%

Procedure

This material was prepared by the reaction (3R)-1-[(7-chlorothieno[3,2-b]pyridin-2-yl)carbonyl]-N,N-dimethylpyrrolidin-3-amine 27a (0.136 g, 0.44 mmole) with 6-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamide 16e (0.064 g, 0.294 mmole) and Cs2CO3 (0.096 g, 0.29 mmole) in a manner as previously described for example 1 to give a brown colored foam (0.059 g, 17%). 1H NMR (300 MHz, CD3OD) δ8.40 (1H, d, J=5.46 Hz), 7.84 (1H, d, J=6.59 Hz), 7.76 (1H, d, J=8.67 Hz), 7.29 (1H, d, J=2.07 Hz), 6.95 (1H, dd, J=8.57, 2.17 Hz), 6.62 (1H, d, J=5.65 Hz), 4.06 (1H, m), 3.87 (2H, m), 3.63 (3H, s) 3.03 (2H, m), 2.88 (3H, s), 2.57 (3H, s), 2.37 (3H, s), 2.32 (3H, s), 2.23 (1H, m), 1.95 (1H, m); HRMS (MH+): Calcd: 492.2085; Found: 492.2069.

Sources & evidence

ORD record
ord-9056942bd7514b2cbd16c57bdd317ab2
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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