1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → HCID 53312354, compound

HRID 2192299Notes

Reaction equation

HRID 2192299 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.[Cl:25][CH2:26][C:27]([NH:29][C:30]1[CH:31]=[N:32][C:33]([CH3:36])=[CH:34][CH:35]=1)=[O:28]>C(#N)C.C(OCC)(=O)C.CCCC(C)C>[Cl-:25].[CH3:36][C:33]1[N:32]=[CH: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][CH:34]=1

Participants

6

Reactant 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 670280112-Chloro-N-(6-methyl-3-pyridinyl)acetamide

Product 1

HCID 53312354HCID 53312354, compoundYield 44.8%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 78922-MethylpentaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 1e)(52 mg) was dissolved in acetonitrile (2 mL) and 2-chloro-N-(6-methylpyridin-3-yl)acetamide (Example f) (29 mg) was added. The reaction mixture was stirred for 10 days and diluted with ethyl acetate (4 mL) and isohexane (14 mL). The mixture was left standing for 5 days, whereupon the resulting crystals were separated and washed with diethyl ether (0.5 mL) to afford the titled compound as a solid (36 mg).

Workup

  1. waitThe mixture was left
  2. waitstanding for 5 days, whereupon the resulting crystals
  3. customwere separated
  4. washwashed with diethyl ether (0.5 mL)

Sources & evidence

ORD record
ord-e43fca0fde604fe89fe0c07d8dbe6950
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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