1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → HCID 67310398, compound

HRID 2192389Notes

Reaction equation

HRID 2192389 reaction equation
[Br:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[N:11][CH:10]=[CH:9][N:8]=1)=[O:6].[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[C@@H:15]([O:21][C:22]([C:24]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23])[CH2:14]2>C(#N)C>[Br-:1].[C:31]1([C:24]2([C:22]([O:21][C@@H:15]3[CH:16]4[CH2:19][CH2:20][N+:13]([CH2:2][CH2:3][NH:4][C:5]([C:7]5[CH:12]=[N:11][CH:10]=[CH:9][N:8]=5)=[O:6])([CH2:18][CH2:17]4)[CH2:14]3)=[O:23])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 67028105HCID 67028105, compound

Product 1

HCID 67310398HCID 67310398, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyrazine-2-carboxylic acid (2-bromo-ethyl)-amide (Example 55a) (87 mg) was added to a solution of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Example 14e) (113 mg) in acetonitrile (2 mL). The reaction mixture was allowed to stir at room temperature for 16 h. A solid precipitated out and was filtered off, washed with cold acetonitrile and dried under vacuum at 40° C. to give the title compound (96 mg) as a white solid.

Workup

  1. customA solid precipitated out and
  2. filtrationwas filtered off
  3. washwashed with cold acetonitrile
  4. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-c50079bf42f9485a96862d0c15fe8aec
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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