Cesium carbonate → 2-Ethyl-6-[(2-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]benzo[b]thiophene-3-carboxylic acid methylamide

HRID 985343Notes

Reaction equation

HRID 985343 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.[CH3:19][NH:20][C:21]([C:23]1[C:24]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:25]=2[S:26][C:27]=1[CH2:28][CH3:29])=[O:22].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:19][NH:20][C:21]([C:23]1[C:24]2[CH:33]=[CH:32][C:31]([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][C@@H:15]([OH:18])[CH2:14]5)=[O:12])[S:10][C:3]=34)=[CH:30][C:25]=2[S:26][C:27]=1[CH2:28][CH3:29])=[O:22]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677587-chloro-2-[(R)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 207677932-Ethyl-6-hydroxybenzo[b]thiophene-3-carboxylic acid methylamide

Product 1

HCID 599908232-Ethyl-6-[(2-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]benzo[b]thiophene-3-carboxylic acid methylamideYield 63.1%

Procedure

This material was prepared by reacting 7-chloro-2-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridine 4a (71 mg, 0.25 mmole) with 2-ethyl-6-hydroxybenzo[b]thiophene-3-carboxylic acid methylamide 134d (71 mg, 0.30 mmole) and Cs2CO3 (244 mg, 0.75 mmole) in a manner analogous to that described for example 1 to give a light brown solid (76 mg, 63%). 1H NMR (DMSO-d6, 300 MHz), δ8.58 (1H, d, J=5.56 Hz), 8.32 (1H, q, J=4.38 Hz), 8.07, 8.00 (1H, s), 7.98 (1H, d, J=2.27 Hz), 7.80 (1H, d, J=8.84 Hz), 7.33 (1H, dd, J=2.27, 8.59 Hz), 6.75 (1H, d, J=5.31 Hz), 4.38, 4.33 (1H, br s), 4.01-3.93 (2H, m), 3.67-3.45 (3H, m), 3.00 (2H, t, J=7.49 Hz), 2.83 (3H, d, J=4.55 Hz), 2.06-1.80 (2H, m), 1.28 (3H, t, J=7.58 Hz).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-286bcf69025e4ea2bc0a4fb91a7a1695
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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