1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → (R)-1-[(6-Methyl-pyrimidin-4-ylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane chloride

HRID 2192397Notes

Reaction equation

HRID 2192397 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]=[C:34]([CH3:36])[N:33]=[CH:32][N:31]=1)=[O:28]>CC#N>[Cl-:25].[CH3:36][C:34]1[N:33]=[CH:32][N:31]=[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])[CH:35]=1

Participants

4

Reactant 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 673110012-Chloro-N-(6-methyl-pyrimidin-4-yl)-acetamide

Product 1

HCID 86655308(R)-1-[(6-Methyl-pyrimidin-4-ylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane chlorideYield 81.2%

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-(6-methyl-pyrimidin-4-yl)-acetamide (Example 59a) (0.36 mmol) in MeCN (2. mL) were stirred together at room temperature for 16 h. 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 (125 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-27f4bda8316b42fea2ff6847c6207e59
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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