1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → HCID 53311102, compound

HRID 2192345Notes

Reaction equation

HRID 2192345 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[CH:35]=[CH:34][N:33]=[CH:32][N:31]=1)=[O:28]>CC#N>[Cl-:25].[C:19]1([C:12]2([C:10]([O:9][C@@H:3]3[CH:4]4[CH2:7][CH2:8][N+:1]([CH2:26][C:27](=[O:28])[NH:29][C:30]5[CH:35]=[CH:34][N:33]=[CH:32][N:31]=5)([CH2:6][CH2:5]4)[CH2:2]3)=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 67030278HCID 67030278, compound

Product 1

HCID 53311102HCID 53311102, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (0.44 mmol) and 2-chloro-N-pyrimidin-4-yl-acetamide (Example 22a) (0.48 mmol) in anhydrous MeCN (2 mL) were stirred together at room temperature for 2.5 days. The reaction mixture was concentrated in vacuo and the residue purified by flash silica gel chromatography (2-10% MeOH/dichloromethane) to give the title compound as a light yellow solid (134 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by flash silica gel chromatography (2-10% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-9fadc5d5d3134e22aa23aa500dab7ba4
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

Loading…