Diethyl Ether → (R)-1-(Pyrazin-2-ylcarbamoylmethyl)-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2192320Notes

Reaction equation

HRID 2192320 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[S:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Br:24][CH2:25][C:26]([NH:28][C:29]1[CH:34]=[N:33][CH:32]=[CH:31][N:30]=1)=[O:27].C(OCC)C.CCCC(C)C>C(#N)C>[Br-:24].[N:30]1[CH:31]=[CH:32][N:33]=[CH:34][C:29]=1[NH:28][C:26]([CH2:25][N+:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2)=[O:27]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 78922-MethylpentaneHCID 445426692-bromo-N-(pyrazin-2-yl)acetamideHCID 58348375HCID 58348375, compound

Product 1

HCID 44516990(R)-1-(Pyrazin-2-ylcarbamoylmethyl)-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Thiophen-2-yl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 5d) (116 mg) and 2-bromo-N-pyrazin-2-yl-acetamide (Example 11a) (75 mg were dissolved in acetonitrile (2 mL) and left overnight. Diethyl ether (10 mL) and isohexane (8 mL) were added and the mixture was left to stand overnight. The resulting crystals were filtered off and washed with diethyl ether to afford the titled compound (117 mg).

Workup

  1. waitthe mixture was left
  2. waitto stand overnight
  3. filtrationThe resulting crystals were filtered off
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-b826ddab0f2d43f5ae29ddb5dc7c5c4e
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

Loading…