1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → HCID 86655302, compound

HRID 2192385Notes

Reaction equation

HRID 2192385 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Cl:25][CH2:26][C:27]([NH:29][C:30]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][N:31]=1)=[O:28]>CC#N>[Cl-:25].[F:36][C:35]1[C:30]([NH:29][C:27]([CH2:26][N+:1]23[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:28])=[N:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 67028934HCID 67028934, compound

Product 1

HCID 86655302HCID 86655302, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Example 14e) (0.30 mmol) and 2-chloro-N-(3-fluoro-pyridin-2-yl)-acetamide (Example 53a) (0.36 mmol) in MeCN (1.5 mL) were stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue purified by silica gel chromatography eluting with 0-10% MeOH/dichloromethane to give the title compound as a white solid (86 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by silica gel chromatography
  3. washeluting with 0-10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-21377254f96145619b18704f126eb639
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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