Diethyl Ether → (R)-1-[(5-Methyl-pyrazin-2-ylcarbamoyl)-methyl]-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2192317Notes

Reaction equation

HRID 2192317 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][C:32]([CH3:35])=[CH:31][N:30]=1)=[O:27].C(OCC)C.CCCC(C)C>C(#N)C>[Br-:24].[CH3:35][C:32]1[N: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][CH:31]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 78922-MethylpentaneHCID 58348375HCID 58348375, compoundHCID 593162612-bromo-N-(5-methylpyrazin-2-yl)acetamide

Product 1

HCID 53311099(R)-1-[(5-Methyl-pyrazin-2-ylcarbamoyl)-methyl]-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromideYield 32.2%

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) (48 mg) was dissolved in acetonitrile (2 mL) and 2-bromo-N-(5-methyl-pyrazin-2-yl)-acetamide (Example 9a) (33 mg) was added. After stirring for 1 week diethyl ether (8 mL) and isohexane (5 mL) were added. The crystals were collected by filtration, washed with ethyl acetate (2×4 mL) and dried to afford the titled compound (26 mg).

Workup

  1. additionwere added
  2. filtrationThe crystals were collected by filtration
  3. washwashed with ethyl acetate (2×4 mL)
  4. customdried

Sources & evidence

ORD record
ord-0f7a9dd4d4264dd4bf1039cf4631148d
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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