HCID 53828382, compound → HCID 13476020, compound

HRID 1247950Notes

Reaction equation

HRID 1247950 reaction equation
N1([C:6]([CH3:16])=[CH:7][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=O)CCCC1.[NH2:17][C:18]1[C:22]([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])=[CH:21][NH:20][N:19]=1>C(O)(=O)C>[CH3:16][C:6]1[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[N:19]2[N:20]=[CH:21][C:22]([C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:24])=[C:18]2[N:17]=1

Participants

4

Reactant 2

HCID 53828382HCID 53828382, compoundHCID 178509267HCID 178509267, compound

Product 1

HCID 13476020HCID 13476020, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.05 mole of 3-(1-pyrrolidinyl)-1-(4-pyridinyl)-2-buten-1-one and 0.05 ml of (3-amino-1H-pyrazol-4-yl)phenyl-methanone in 50 ml of glacial acetic acid was refluxed for 8 hours. The solvent was removed and the residue partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The dichloromethane layer was washed with water, dried over magnesium sulfate and passed through a short pad of hydrous magnesium silicate. The eluent was concentrated and the residue crystallized from dichloromethane:hexane, giving the desired product, mp 209°-210° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customThe solvent was removed
  3. customthe residue partitioned between saturated aqueous sodium bicarbonate and dichloromethane
  4. washThe dichloromethane layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe eluent was concentrated
  7. customthe residue crystallized from dichloromethane

Sources & evidence

ORD record
ord-c8a1d8c784c44ec398f4b44f0b6f7191
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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