2-(2-Bromoethyl)pyrazine → (R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-(2-pyrazin-2-yl-ethyl)-azonia-bicyclo[2.2.2]octane bromide

HRID 2192356Notes

Reaction equation

HRID 2192356 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1.[N:10]12[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]1)[C@@H:12]([O:18][C:19]([C:21]1([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20])[CH2:11]2>C(#N)C>[Br-:1].[C:28]1([C:21]2([C:19]([O:18][C@@H:12]3[CH:13]4[CH2:16][CH2:17][N+:10]([CH2:2][CH2:3][C:4]5[CH:9]=[N:8][CH:7]=[CH:6][N:5]=5)([CH2:15][CH2:14]4)[CH2:11]3)=[O:20])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 583484082-(2-Bromoethyl)pyrazineHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 67027769(R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-(2-pyrazin-2-yl-ethyl)-azonia-bicyclo[2.2.2]octane bromideYield 38.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(2-Bromo-ethyl)-pyrazine (Example 32a) (43 mg) was added to a solution of 1-phenyl -cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (50 mg) in acetonitrile (1 mL). The reaction mixture was allowed to stir at room temperature for 68 h. The volatiles were evaporated and the product was purified by silica gel chromatography eluting with 0-20% MeOH/dichloromethane. The relevant fractions were combined and concentrated, dissolved up in dichloromethane, filtered and evaporated to give the title compound (30 mg) as a yellow gummy glass.

Workup

  1. customThe volatiles were evaporated
  2. customthe product was purified by silica gel chromatography
  3. washeluting with 0-20% MeOH/dichloromethane
  4. concentrationconcentrated
  5. dissolutiondissolved up in dichloromethane
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8420b91194dc42b08cf0ffaac144fefa
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

Loading…