Cesium carbonate → 6-[(2-([(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]carbonyl)thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylic acid cyclopropylamide

HRID 985324Notes

Reaction equation

HRID 985324 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.[CH:21]1([NH:24][C:25]([C:27]2[C:28]3[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][C:29]=3[S:30][C:31]=2[CH3:32])=[O:26])[CH2:23][CH2:22]1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH:21]1([NH:24][C:25]([C:27]2[C:28]3[CH:36]=[CH:35][C:34]([O:37][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][CH2:15][C@H:14]6[CH2:18][O:19][CH3:20])=[O:12])[S:10][C:3]=45)=[CH:33][C:29]=3[S:30][C:31]=2[CH3:32])=[O:26])[CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677647-chloro-2-[(S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 20767913N-cyclopropyl-6-hydroxy-2-methylbenzo[b]thiophene-3-carboxamide

Product 1

HCID 599907586-[(2-([(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]carbonyl)thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylic acid cyclopropylamideYield 70%

Procedure

This material was prepared by the reaction of 7-chloro-2-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridine 2a (124 mg, 0.40 mmole) with 6-hydroxy-2-methylbenzo[b]thiophene-3-carboxylic acid cyclopropylamide 8c (119 mg, 0.48 mmole) and Cs2CO3 (391 mg, 1.2 mmole) in a manner as previously described for example 1 to give a yellow solid (146 mg, 70%). 1H NMR (DMSO-d6, 300 MHz) δ8.58 (1H. d, J=5.27 Hz), 8.46 (1H, d, J=4.33 Hz), 8.03 (1H, s), 7.96 (1H, d, J=2.26 Hz), 7.80 (1H, d, J=8.67 Hz), 7.32 (1H, dd, J=2.17, 8.76 Hz), 6.75 (1H, d, J=5.27 Hz), 4.30 (1H, m), 3.84 (2H, m), 3.53 (1H, m) 3.42 (1H, m), 3.27 (3H, s), 2.89 (1H, m), 2.57 (3H, s), 2.09-1.81 (4H, m) 0.72 (2H, m), 0.59 (2H, m).

Sources & evidence

ORD record
ord-080ca2d684f040378b41e2d05711c579
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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