2-Methylpentane → (R)-1-(Pyridazin-3-ylcarbamoylmethyl)-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2192310Notes

Reaction equation

HRID 2192310 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[N:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:27].C(OCC)(=O)C.CCCC(C)C>C(#N)C>[Br-:24].[N:31]1[CH:32]=[CH:33][CH:34]=[C:29]([NH:28][C:26]([CH2:25][N+:1]23[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:27])[N:30]=1

Participants

6

Reactant 4

HCID 78922-MethylpentaneHCID 8857Ethyl AcetateHCID 574315532-Bromo-N-pyridazin-3-yl-acetamideHCID 58348375HCID 58348375, compound

Product 1

HCID 44516986(R)-1-(Pyridazin-3-ylcarbamoylmethyl)-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromideYield 10.6%

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) (80 mg) and 2-bromo-N-pyridazin-3-yl-acetamide (Example 5e) (52 mg) were dissolved in acetonitrile (3 mL) and stirred overnight. Ethyl acetate (9 mL) and isohexane (4 mL) were added and stirred overnight. The resulting crystals were filtered off and then triturated with ethyl acetate to afford the titled compound (14 mg).

Workup

  1. stirringstirred overnight
  2. filtrationThe resulting crystals were filtered off
  3. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-c6bfc223041e4668b782e43772e947d5
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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