Ammonia → HCID 53991038, compound

HRID 2254050Notes

Reaction equation

HRID 2254050 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-70e1e679822d4bf29784f1e79c0fa6ad
Source dataset
uspto-grants-1993_08
Patent number
US05234930

Reaction notes

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