Cesium carbonate → 6-{[2-(Azetidin-1-ylcarbonyl)thieno[3,2-b]pyridin-7-yl]oxy)-2-ethylbenzo[b]thiophene-3-carboxylic acid methylamide

HRID 985345Notes

Reaction equation

HRID 985345 reaction equation
[N:1]1([C:5]([C:7]2[S:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3Cl)[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH3:17][NH:18][C:19]([C:21]1[C:22]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:23]=2[S:24][C:25]=1[CH2:26][CH3:27])=[O:20].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:17][NH:18][C:19]([C:21]1[C:22]2[CH:31]=[CH:30][C:29]([O:32][C:13]3[CH:12]=[CH:11][N:10]=[C:9]4[CH:8]=[C:7]([C:5]([N:1]5[CH2:4][CH2:3][CH2:2]5)=[O:6])[S:15][C:14]=34)=[CH:28][C:23]=2[S:24][C:25]=1[CH2:26][CH3:27])=[O:20]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677932-Ethyl-6-hydroxybenzo[b]thiophene-3-carboxylic acid methylamideHCID 221435492-(Azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridine

Product 1

HCID 207678536-{[2-(Azetidin-1-ylcarbonyl)thieno[3,2-b]pyridin-7-yl]oxy)-2-ethylbenzo[b]thiophene-3-carboxylic acid methylamideYield 66.4%

Procedure

This material was prepared by reacting 2-(azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridine 25a (97 mg, 0.40 mmole) with 2-ethyl-6-hydroxybenzo[b]thiophene-3-carboxylic acid methylamide 134d (113 mg, 0.48 mmole) and Cs2CO3 (391 mg, 1.2 mmole)in a manner similar to that previously described for example 1 to give a yellow solid (120 mg, 52%). 1H NMR (DMSO-d6, 300 MHz) δ8.59 (1H, d, J=5.67 Hz), 8.31 (1H, m), 7.98 (1H, d, J=2.27 Hz), 7.89 (1H, s), 7.81 (1H, d, J=8.69 Hz), 7.33 (1H, dd, J=1.51, 8.69 Hz), 6.76 (1H, d, J=5.29 Hz), 4.62 (2H, t, J=7.37 Hz), 4.11 (2H, t, J=7.37 Hz), 3.00 (2H, q, J=7.55 Hz), 2.83 (3H, d, J=4.53 Hz), 2.35 (2H, m), 1.28 (3H, t, J=7.55 Hz).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-7a37f9f79b0c47d5852bfd693bba8269
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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