Ammonia → HCID 53991038, compound

HRID 263544Notes

Reaction equation

HRID 263544 reaction equation
S(Cl)(Cl)=O.C(Cl)Cl.[C:8]1([C:14]2[C:22]([CH:23]=[CH:24][C:25]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][C@@H:28]3[CH2:33][C:34]([OH:36])=O)=[O:26])=[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N:16]3[N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH3:37]>CN(C)C=O>[C:8]1([C:14]2[C:22]([CH:23]=[CH:24][C:25]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][C@@H:28]3[CH2:33][C:34](=[O:36])[NH2:37])=[O:26])=[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N:16]3[N:15]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 177807HCID 177807, compound

Product 1

HCID 53991038HCID 53991038, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (0.2 ml) was added dropwise to a solution of methylene chloride (dry, 40 ml) and N,N-dimethylformamide (0.2 ml) at 0° C. and stirred for 30 minutes. To this cooled solution was added (2R)-1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-(carboxymethyl)piperidine (trans isomer) (1.0 g) and the mixture was stirred for 1.5 hours. To this solution was added a solution of 28% aqueous ammonia solution (20 ml) and stirring was continued for further 2 hours. The aqueous and organic phases were separated and the organic layer was evaporated. The oily residue was subjected to column chromatography (silica gel, 60 mesh) using ethyl acetate as eluent. Evaporation of the solvent afforded (2R)-1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-(carbamoylmethyl)piperidine (trans isomer) (405 mg) as a white granular solid.

Workup

  1. stirringthe mixture was stirred for 1.5 hours
  2. stirringstirring
  3. waitwas continued for further 2 hours
  4. customThe aqueous and organic phases were separated
  5. customthe organic layer was evaporated
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-70c836cc2a894c83ada7dc6fd2b2d2ca
Source dataset
uspto-grants-1997_07
Patent number
US05643938

Reaction notes

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