Diethyl Ether → HCID 86655277, compound

HRID 2192339Notes

Reaction equation

HRID 2192339 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=[O:4].[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@@H:14]([O:20][C:21]([C:23]1([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])[CH2:13]2.C(OCC)C>C(#N)C>[Cl-:1].[C:30]1([C:23]2([C:21]([O:20][C@@H:14]3[CH:15]4[CH2:18][CH2:19][N+:12]([CH2:2][C:3](=[O:4])[NH:5][C:6]5[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=5)([CH2:17][CH2:16]4)[CH2:13]3)=[O:22])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 43824892-chloro-N-(pyridin-4-yl)acetamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 86655277HCID 86655277, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-N-pyridin-4-yl-acetamide (Example 16a) (30 mg) was added to a solution of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (53 mg) in acetonitrile (1 mL). The reaction mixture was stirred at room temperature for 24 h. Diethyl ether (2 mL) was added and the reaction mixture was filtered to give a light brown solid. The solid was washed several times with diethyl ether and dried under vacuum at 40° C. Purification by column chromatography eluting with 0-10% MeOH/ dichloromethane gave the title compound as a white solid (20 mg).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto give a light brown solid
  3. washThe solid was washed several times with diethyl ether
  4. customdried under vacuum at 40° C
  5. customPurification by column chromatography
  6. washeluting with 0-10% MeOH/ dichloromethane

Sources & evidence

ORD record
ord-f230f70bf7cf402590b9c1dc0a7d7dd5
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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