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

HRID 985260Notes

Reaction equation

HRID 985260 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.[OH:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([C:26]1[C:34]2[C:29](=[CH:30][C:31]([OH:35])=[CH:32][CH:33]=2)[N:28]([CH3:36])[C:27]=1[CH3:37])=[O:25].C([O-])([O-])=O.[Cs+].[Cs+]>>[OH:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([C:26]1[C:34]2[C:29](=[CH:30][C:31]([O:35][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][C@@H:15]([OH:18])[CH2:14]5)=[O:12])[S:10][C:3]=34)=[CH:32][CH:33]=2)[N:28]([CH3:36])[C:27]=1[CH3:37])=[O:25]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677587-chloro-2-[(R)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 207678646-Hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

Product 1

HCID 599908036-[2-((R)-3-Hydroxy-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

Procedure

This material was prepared by the reaction of (7-chloro-thieno [3,2-b] pyridin-2-yl)-((R)-3-hydroxy-pyrrolidin-1-yl)-methanone 4a 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) δ8.38 (1H, d, J=5.5 Hz), 7.84-7.74 (2H, m), 7.28 (1H, d, J=2.1 Hz), 6.94 (1H, dd, J=2.1, 8.6 Hz), 6.60 (1H, d, J=5.5 Hz), 4.45-4.42 (1H, m), 3.93-3.91 (2H, m), 3.71-3.60 (8H, m), 3.45 (2H, m), 2.56 (3H, s), 2.02-1.98 (2H, m), 1.72-1.68 (2H, m). LCMS (ESI+) [M+H]/z Calc'd 509, found 509.

Sources & evidence

ORD record
ord-292ba316b6eb4e44a30c304e94a937f6
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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