4-(2-Pyrrolidin-1-ylethoxymethyl)piperidine → 3-Phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-b]pyridine

HRID 928575Notes

Reaction equation

HRID 928575 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[S:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:3]=12.[N:17]1([CH2:22][CH2:23][O:24][CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH2:21][CH2:20][CH2:19][CH2:18]1>>[C:11]1([C:10]2[C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[N:29]3[CH2:30][CH2:31][CH:26]([CH2:25][O:24][CH2:23][CH2:22][N:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)[CH2:27][CH2:28]3)[S:8][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineHCID 684343754-Chloro-3-phenylthieno[2,3-b]pyridine

Product 1

HCID 895796443-Phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-b]pyridineYield 10.8%

Conditions

Temperature
170 °C

Procedure

4-Chloro-3-phenyl-thieno[2,3-b]pyridine (150 mg, 0.462 mmol) and 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine (150 mg, 0.706 mmol) were combined and heated in a Reactivial at 170° C. overnight. The reaction mixture was allowed to cool to room temperature and purified by basic prep HPLC to afford 3-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-b]pyridine (21 mg). LCMS [M+H]=422.2

Workup

  1. temperatureto cool to room temperature
  2. custompurified by basic prep HPLC

Sources & evidence

ORD record
ord-f49dbaee73774912af2c8e6e17e34f55
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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