Cesium carbonate → 6-[2-(3-Hydroxy-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-1,2-dimethyl-3H-indole-3-carboxylic acid propylamide

HRID 1825134Notes

Reaction equation

HRID 1825134 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]([OH:18])[CH2:14]3)=[O:12])[S:10][C:3]=12.[CH2:19]([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])[CH2:20][CH3:21].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:19]([NH:22][C:23]([CH: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][CH:15]([OH:18])[CH2:14]5)=[O:12])[S:10][C:3]=34)=[CH:31][CH:32]=2)[N:27]([CH3:35])[CH:26]1[CH3:36])=[O:24])[CH2:20][CH3:21]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677587-chloro-2-[(R)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 221436346-Hydroxy-1,2-dimethyl-1H-indol-3-carboxylic acid propylamide

Product 1

HCID 693680506-[2-(3-Hydroxy-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-1,2-dimethyl-3H-indole-3-carboxylic acid propylamide

Procedure

This material was prepared by the reaction of 7-chloro-2-[(R)-3-hydroxypyrrolidine-1-carbynyl]thieno[3,2,-b]pyridine 4a with 6-hydroxy-1,2-dimethyl-1H-indol-3-carboxylic acid propylamide 58b and Cs2CO3 in a manner as previously described for example 1. 1H NMR (300 MHz, CD3OD) δ 8.50 (1H, d, J=5.6 Hz), 7.96 (1H, d, J=17.3 Hz), 7.86 (1H, d, J=8.7 Hz), 7.40 (1H, s), 7.06 (1H, d, J=10.7 Hz), 6.72 (1H, d, J=5.6 Hz), 4.61–4.53 (1H, m), 4.15–4.00 (2H, m), 3.91–3.73 (3H, m), 3.73 (3H, s), 3.53–3.40 (2H, m), 2.67 (3H, s), 2.28–2.07 (2H, m), 1.78–1.69 (2H, m), 1,18–1.04 (3H, m). LCMS (ESI+) [M+H]1z Calc'd 493. found 493.

Sources & evidence

ORD record
ord-e24cc5e0a80046e3b5eaccc90f8fb5dc
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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