Cesium carbonate → 1,2-Dimethyl-6-[2-(pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

HRID 985261Notes

Reaction equation

HRID 985261 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][CH2:15][CH2:14]3)=[O:12])[S:10][C:3]=12.[OH:18][CH2:19][CH2:20][CH2:21][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+]>>[OH:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([C:25]1[C:33]2[C:28](=[CH:29][C:30]([O:34][C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[C:9]([C:11]([N:13]5[CH2:17][CH2:16][CH2:15][CH2:14]5)=[O:12])[S:10][C:3]=34)=[CH:31][CH:32]=2)[N:27]([CH3:35])[C:26]=1[CH3:36])=[O:24]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 11173165(7-Chlorothieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanoneHCID 207678646-Hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

Product 1

HCID 207678961,2-Dimethyl-6-[2-(pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

Procedure

This material was prepared from the reaction of (7-chloro-thieno[3,2-b]pyridin-2-yl)-pyrrolidin-1-yl-methanone with 6-hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide 63b and Cs2CO3 in a manner as previously described for example 1. 1H NMR (300 MHz, CD3OD) δ8.44 (1H, d, J=5.5 Hz), 7.85 (1H, s), 7.83 (1H, d, J=10.0 Hz), 7.35 (1H, d, J=1.9 Hz), 7.01 (1H, dd, J=1.9, 8.5 Hz), 6.66 (1H, d, J=5.5 Hz), 3.88 (2H, m), 3.67 (7H, m), 3.54 (2H, m), 2.63 (3H, s), 1.83-2.10 (6H, m). LCMS (ESI+) [M+H]/z Calc'd 493, found 493.

Sources & evidence

ORD record
ord-a09d731cd6e5455bb56bd7bc7acd69e3
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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