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 1825098ノート

反応式

HRID 1825098 の反応式
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.[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])[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:21][C:22]3[CH:30]=[C:29]4[C:25]([C:26]([C:33]([NH:35][CH3:36])=[O:34])=[C:27]([CH3:32])[N:28]4[CH3:31])=[CH:24][CH:23]=3)[CH:8]=2)=[O:12])[CH2:14]1

参加物

4

反応物 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

生成物 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-carboxamide収率 40.8%

実験手順

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 (0.0649, 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) δ 8.40 (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.

出典と根拠

ORDレコード
ord-1a79ca5897be46eda02f8c2510a94113
出典データセット
uspto-grants-2006_05
特許番号
US07045528B2

反応ノート

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