Ammonia → HCID 18182297, compound

HRID 1359404Notes

Reaction equation

HRID 1359404 reaction equation
FC(F)(F)S(O[C:7]1[N:12]=[N:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][C:8]=1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)=O.[C:28]([C:30]1([OH:38])[CH:35]2[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]2)[CH2:31]1)#[CH:29].C(N(CC)CC)C.N>CN(C)C=O>[C:13]1([C:10]2[N:11]=[N:12][C:7]([C:29]#[C:28][C:30]3([OH:38])[CH:35]4[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]4)[CH2:31]3)=[C:8]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:9]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 18182180HCID 18182180, compound

Product 1

HCID 18182297HCID 18182297, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 484 mg of 3-phenyl-5-benzyl-6-pyridazyl trifluoromethane sulfonate, 223 mg of 3-ethynyl-3-quinuclidinol, 284 mg of tetrakis (triphenylphosphine)palladium(0), 47 mg of cuprous iodide, 513 μl of triethylamine and 5.0 ml of N,N-dimethylformamide was heated under stirring at 80° C. for 2 hours in a nitrogen atmosphere. The reaction solution was poured into aqueous dilute ammonia and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and the solvent was removed. The residue was subjected to NH-silica gel (Fuji Silicia) column chromatography and eluted with hexane/ethyl acetate (1:1) and then with ethyl acetate/methanol (20:1) and then crystallized from hexane/ethyl acetate, to give 413 mg of the target compound.

Workup

  1. temperaturewas heated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. customthe solvent was removed
  5. washeluted with hexane/ethyl acetate (1:1)
  6. customwith ethyl acetate/methanol (20:1) and then crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-d1aa24baa5b84781ae9aa4a479361d4f
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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