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

HRID 985344Notes

Reaction equation

HRID 985344 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][C@H:14]3[CH2:18][O:19][CH3:20])=[O:12])[S:10][C:3]=12.[CH3:21][NH:22][C:23]([C:25]1[C:26]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][C:27]=2[S:28][C:29]=1[CH2:30][CH3:31])=[O:24].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:21][NH:22][C:23]([C:25]1[C:26]2[CH:35]=[CH:34][C:33]([O:36][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][C@H:14]5[CH2:18][O:19][CH3:20])=[O:12])[S:10][C:3]=34)=[CH:32][C:27]=2[S:28][C:29]=1[CH2:30][CH3:31])=[O:24]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677647-chloro-2-[(S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 207677932-Ethyl-6-hydroxybenzo[b]thiophene-3-carboxylic acid methylamide

Product 1

HCID 599908072-Ethyl-6-[(2-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl)thieno[3,2-b]pyridin-7-yl)oxy]benzo[b]thiophene-3-carboxylic acid methylamideYield 10%

Procedure

This material was prepared by reacting 7-chloro-2-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridine 2a (155 mg, 0.5 mmole) with 2-ethyl-6-hydroxybenzo[b]thiophene-3-carboxylic acid methylamide 134d (141 mg, 0.60 mmole) and Cs2CO3 (488 mg, 1.5 mmole) in a manner analogous to that described for example 1 to give a yellow solid (25 mg, 10%). 1H NMR (DMSO-d6, 300 MHz), δ8.59 (1H, d, J=5.56 Hz), 8.33 (1H, d, J=4.55 Hz), 8.03 (1H, s), 7.99 (1H, d, J=2.02 Hz), 7.81 (1H, d, J=8.59 Hz), 7.33 (1H, dd, J=2.27, 8.84 Hz), 6.77 (1H, d, J=5.56 Hz), 4.31 (1H, br s), 3.90-3.81 (2H, m), 3.37-3.15 (2H, m), 3.37 (3H, s), 3.00 (2H, q, J=7.41 Hz), 2.83 (3H, d, J=4.55 Hz), 2.09-1.84 (4H, m), 1.28 (3H, t, J=7.58 Hz).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-336dd7bac5164343bfa741d90b1e82e7
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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