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

HRID 985249Notes

Reaction equation

HRID 985249 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.[CH:19]1([NH:22][C:23]([C:25]2[C:33]3[C:28](=[CH:29][C:30]([OH:34])=[CH:31][CH:32]=3)[N:27]([CH3:35])[C:26]=2[CH3:36])=[O:24])[CH2:21][CH2:20]1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH:19]1([NH:22][C:23]([C:25]2[C:33]3[C:28](=[CH:29][C:30]([O:34][C:2]4[CH:7]=[CH:6][N:5]=[C:4]5[CH:8]=[C:9]([C:11]([N:13]6[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14]6)=[O:12])[S:10][C:3]=45)=[CH:31][CH:32]=3)[N:27]([CH3:35])[C:26]=2[CH3:36])=[O:24])[CH2:20][CH2:21]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677587-chloro-2-[(R)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 221435471,2-dimethyl-6-hydroxy-1H-indole-3-carboxylic acid cyclopropylamide

Product 1

HCID 599907826-[2-((R)-3-Hydroxy-pyrrol idine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-1,2-dimethyl-1H-indole-3-carboxylic acid cyclopropylamide

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 cyclopropylamide 20b and Cs2CO3 in a manner as previously described for example 1. 1H NMR (300 MHz, CD3OD) δ8.50 (1H, d, J=5.5 Hz), 7.93 (1H, d, J=17.33 Hz), 7.80 (1H, d, J=8.6 Hz), 7.39 (1H, d, J=2.1 Hz), 7.05 (1H, dd, J=2.1, 8.6 Hz), 6.71 (1H, d, J=5.5 Hz), 4.54 (1H, bs), 4.11-4.00 (2H, m), 3.85-3.72 (6H, m), 2.93-2.86 (1H, m), 2.66 (3H, s), 2.19-2.07 (2H, m), 0.90-0.84 (2H, m), 0.76-0.68 (2H, m). LCMS (ESI+) [M+H]/z Calc'd 491, found 491.

Sources & evidence

ORD record
ord-dccf2e07621f4fd2a49553d040d07ee1
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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