Ammonia → HCID 18182468, compound

HRID 1359316Notes

Reaction equation

HRID 1359316 reaction equation
CN(C)C=O.FC(F)(F)S(O[C:12]1[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][C:15]([C:25]([O:27][CH3:28])=[O:26])=[CH:14][N:13]=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].N>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:18]([C:17]1[C:12]([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:13][CH:14]=[C:15]([C:25]([O:27][CH3:28])=[O:26])[CH:16]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 18182323HCID 18182323, compound

Product 1

HCID 18182468HCID 18182468, compoundYield 59.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

50 ml of N,N-dimethylformamide was added to a mixture of 2.0 g of 3-benzyl-5-methoxycarbonyl-2-pyridyl trifluoromethanesulfonate, 742 mg of 3-ethynyl-3-quinuclidinol, 1.5 g of tetrakis(triphenylphosphine)palladium(0), 374 mg of cuprous iodide and 2.7 ml of triethylamine, followed by heating under stirring for one hour in an oil bath kept at 60° C. 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 magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using chloroform/methanol/aqueous 36% ammonia (46:3:0.3) as an eluent for separation and purification, to give 1.1 g of the target compound.

Workup

  1. temperatureby heating
  2. customkept at 60° C. in a nitrogen atmosphere
  3. temperatureAfter cooling as it
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was further washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed
  8. customfor separation and purification

Sources & evidence

ORD record
ord-089a21d1209446f68245274b607117e1
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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