Cesium carbonate → 6-({2-[4(Hydroxymethyl)-1,3-thiazol-2-yl]thieno[3,2-b]pyridin-7-yl}oxy)-2-methylbenzo[b]thiophene-3-carboxylic acid cyclopropylamide

HRID 1825223Notes

Reaction equation

HRID 1825223 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=3)[S:10][C:3]=12.[CH:18]1([NH:21][C:22]([C:24]2[C:25]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:26]=3[S:27][C:28]=2[CH3:29])=[O:23])[CH2:20][CH2:19]1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH:18]1([NH:21][C:22]([C:24]2[C:25]3[CH:33]=[CH:32][C:31]([O:34][C:2]4[CH:7]=[CH:6][N:5]=[C:4]5[CH:8]=[C:9]([C:11]6[S:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=6)[S:10][C:3]=45)=[CH:30][C:26]=3[S:27][C:28]=2[CH3:29])=[O:23])[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 20767913N-cyclopropyl-6-hydroxy-2-methylbenzo[b]thiophene-3-carboxamideHCID 22143517[2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-thiazol-4-yl]-methanol

Product 1

HCID 207679126-({2-[4(Hydroxymethyl)-1,3-thiazol-2-yl]thieno[3,2-b]pyridin-7-yl}oxy)-2-methylbenzo[b]thiophene-3-carboxylic acid cyclopropylamideYield 44%

Procedure

This material was prepared by reacting [2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazol-4-yl]methanol (124 mg, 0.5 mmole) with 6-hydroxy-2-methylbenzo[b]thiophene-3-carboxylic acid cyclopropylamide 8c (113 mg, 0.4 mmole) and Cs2CO3 (391 mg, 1.2 mmole) in a manner similar to that previously described for example 1 to give a yellow solid (86 mg, 44%). 1H NMR (DMSO-d6, 300 MHz) δ 8.56 (1H, d, J=5.4 Hz), 8.46 (1H, d, J=4.3 Hz), 8.17 (1H, s), 7.96 (1H, d, J=2.2 Hz), 7.81 (1H, d, J=8.8 Hz), 7.63 (1H, s), 7.34 (1H, dd, J=2.2, 8.8 Hz), 6.75 (1H, d, J=5.4 Hz), 4.60 (2H, d, J=4.9 Hz), 2.96–2.85 (1H, m), 2.57 (3H, s), 0.78–0.67 (2H, m), 0.62–0.53 (2H, m).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-e263ddc9acf941ad9a5c81cc69ab9be0
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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