2-chloro-N-(5-cyano-2-pyridinyl)acetamide → (R)-1-[(5-Cyano-pyridin-2-ylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane chloride

HRID 2192381Notes

Reaction equation

HRID 2192381 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][C:33]([C:36]#[N:37])=[CH:32][N:31]=1)=[O:28]>CC#N>[Cl-:25].[C:36]([C:33]1[CH:34]=[CH:35][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]=1)#[N:37]

Participants

4

Reactant 2

HCID 445742932-chloro-N-(5-cyano-2-pyridinyl)acetamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 86655299(R)-1-[(5-Cyano-pyridin-2-ylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane chlorideYield 38.2%

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-(5-cyano-pyridin-2-yl)-acetamide (Example 51a) (0.36 mmol) in MeCN (1.5 mL) were stirred together 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 (60 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-6fc97a2179c74c5d96599691be70ac8b
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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