6-Methoxy-2-[4-(2-(1-pyrrolidinyl)ethoxy)phenyl]benzo[b]thiophene → (+/-)-6-Hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 6-[[trans-2-(1-Piperidyl)cyclohexyl]oxy]pyrid-3-yl Ketone

HRID 1387005Notes

Reaction equation

HRID 1387005 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:13][CH:12]=3)[S:8][C:7]=2[CH:25]=1.[N:26]1([C@@H:32]2[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]2[O:38][C:39]2[N:44]=[CH:43][C:42]([C:45](O)=[O:46])=[CH:41][CH:40]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>>[N:26]1([C@@H:32]2[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]2[O:38][C:39]2[N:44]=[CH:43][C:42]([C:45]([C:10]3[C:6]4[CH:5]=[CH:4][C:3]([OH:2])=[CH:25][C:7]=4[S:8][C:9]=3[C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:15][CH:16]=3)=[O:46])=[CH:41][CH:40]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 106894206-Methoxy-2-[4-(2-(1-pyrrolidinyl)ethoxy)phenyl]benzo[b]thiopheneHCID 18397566(+/-)-6-[[trans-2-(1-Piperidyl)cyclohexyl]oxy]-3-pyridinecarboxylic acid

Product 1

HCID 18397503(+/-)-6-Hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 6-[[trans-2-(1-Piperidyl)cyclohexyl]oxy]pyrid-3-yl KetoneYield 29%

Procedure

The title compound was prepared in 29% yield from 6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (Example 1, Part B) and (±)-6-[[trans-2-(1-piperidyl)cyclohexyl]oxy]-3-pyridinecarboxylic acid (Part A) by essentially following the procedures detailed in Example 20, Parts D and E.

Sources & evidence

ORD record
ord-0b11c17c3cee4d809e36ad5169f13011
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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