1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → HCID 53312356, compound

HRID 2192301Notes

Reaction equation

HRID 2192301 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[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Br:25][CH2:26][C:27]([NH:29][C:30]1[CH:35]=[N:34][CH:33]=[C:32]([CH3:36])[N:31]=1)=[O:28]>C(#N)C>[Br-:25].[CH3:36][C:32]1[N:31]=[C:30]([NH:29][C:27]([CH2:26][N+:1]23[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:28])[CH:35]=[N:34][CH:33]=1

Participants

4

Reactant 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 67028088HCID 67028088, compound

Product 1

HCID 53312356HCID 53312356, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 1e) (70 mg) and 2-bromo-N-(6-methylpyrazin-2-yl) acetamide (Example 2a) (49.2 mg) were dissolved in acetonitrile (1 mL) and left to stand overnight. Crystals separated on standing and were filtered and washed with acetonitrile (2×1 mL), ethyl acetate (2×3 mL) and diethyl ether (2×3 mL) and dried to yield the titled compound (24 mg).

Workup

  1. waitleft
  2. customCrystals separated on standing
  3. filtrationwere filtered
  4. washwashed with acetonitrile (2×1 mL), ethyl acetate (2×3 mL) and diethyl ether (2×3 mL)
  5. customdried

Sources & evidence

ORD record
ord-b0d64662a3804dbdafa81b6287dddac8
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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