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

HRID 2192311Notes

Reaction equation

HRID 2192311 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:33]=[C:32]([CH3:34])[O:31][N:30]=1)=[O:27].C(OCC)(=O)C.CCCC(C)C>C(#N)C>[Br-:24].[CH3:34][C:32]1[O:31][N:30]=[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])[CH:33]=1

Participants

6

Reactant 4

HCID 78922-MethylpentaneHCID 8857Ethyl AcetateHCID 64850652-Bromo-N-(5-methyl-isoxazol-3-yl)-acetamideHCID 58348375HCID 58348375, compound

Product 1

HCID 44516988(R)-1-[(5-Methyl-isoxazol-3-ylcarbamoyl)-methyl]-3-(1-thiophen-2-yl cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromideYield 72.8%

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) (68 mg) and 2-bromo-N-(5-methyl-isoxazol-3-yl)-acetamide (Example 6a) (45 mg) were dissolved in acetonitrile (2 mL) and stirred overnight. Ethyl acetate (10 mL) and isohexane (9 mL) were added and stirred overnight. The resulting crystals were filtered off and washed with ethyl acetate to afford the titled compound (82 mg).

Workup

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

Sources & evidence

ORD record
ord-9b6781f2289446baa88bd09cf5bb0acd
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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