Ammonia → HCID 18182230, compound

HRID 1359314Notes

Reaction equation

HRID 1359314 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][C:10]([C:20](=[O:28])[NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:9][N:8]=1)(=O)=O.[C:31]([C:33]1([OH:41])[CH:38]2[CH2:39][CH2:40][N:35]([CH2:36][CH2:37]2)[CH2:34]1)#[CH:32].C(N(CC)CC)C.N>CN(C)C=O>[CH2:13]([C:12]1[C:7]([C:32]#[C:31][C:33]2([OH:41])[CH:38]3[CH2:39][CH2:40][N:35]([CH2:36][CH2:37]3)[CH2:34]2)=[N:8][CH:9]=[C:10]([C:20](=[O:28])[NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:11]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 18182242HCID 18182242, compound

Product 1

HCID 18182230HCID 18182230, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg of 3-benzyl-5-(N-phenylcarbamoyl)-2-pyridyl trifluoromethanesulfonate, 60 mg of 3-ethynyl-3-quinuclidinol, 50 mg of tetrakis (triphenylphosphine)palladium(0), 10 mg of cuprous iodide and 0.15 ml of triethylamine were added to 2 ml of N,N-dimethylformamide, followed by stirring for 3 hours in an oil bath kept at 50° C. After cooling as it was, aqueous ammonia was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to NH-silica gel column chromatography, to synthesize 90 mg of the target compound.

Workup

  1. customkept at 50° C
  2. temperatureAfter cooling as it
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto synthesize 90 mg of the target compound

Sources & evidence

ORD record
ord-6257a7ed302e45bb9d9ceb6bfa74bc9d
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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