Ammonia → HCID 18182340, compound

HRID 1359425Notes

Reaction equation

HRID 1359425 reaction equation
CN(C)C=O.[CH2:6]([C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]3[O:25][CH2:26][O:27][C:21]=3[CH:20]=2)[S:16][C:17]=1Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[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].N>C(OCC)(=O)C.C(N(CC)CC)C>[CH2:6]([C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]3[O:25][CH2:26][O:27][C:21]=3[CH:20]=2)[S:16][C:17]=1[C:29]#[C:28][C:30]1([OH:38])[CH:35]2[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]2)[CH2:31]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 18182198HCID 18182198, compound

Product 1

HCID 18182340HCID 18182340, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

5 ml of N,N-dimethylformamide was added to a mixture of 377 mg of 4-benzyl-5-bromo-2-(3,4-methylenedioxyphenyl)thiazole, 178 mg of 3-ethynyl-3-quinuclidinol, 68 mg of tetrakis (triphenylphosphine)palladium(0), 18 mg of cuprous iodide and 0.5 ml of triethylamine, followed by heating under stirring at 100° C. in an oil bath for 15 minutes in a nitrogen atmosphere. After cooling as it was, ethyl acetate and aqueous ammonia were added thereto, and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The resulting crystals were collected by filtration, to give 253 mg of the target compound.

Workup

  1. temperatureby heating
  2. temperatureAfter cooling as it
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was further washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed
  7. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-299f453fb4d44e8b97341d9032e6611a
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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