HCID 54179722, compound → N-[3-(3-Benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]propanamide

HRID 1247974Notes

Reaction equation

HRID 1247974 reaction equation
[NH2:1][C:2]1[C:6]([C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][NH:4][N:3]=1.CN(C)[CH:17]=[CH:18][C:19]([C:21]1[CH:22]=[C:23]([NH:27][C:28](=[O:31])[CH2:29][CH3:30])[CH:24]=[CH:25][CH:26]=1)=O>C(O)(=O)C>[C:7]([C:6]1[CH:5]=[N:4][N:3]2[C:19]([C:21]3[CH:22]=[C:23]([NH:27][C:28](=[O:31])[CH2:29][CH3:30])[CH:24]=[CH:25][CH:26]=3)=[CH:18][CH:17]=[N:1][C:2]=12)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 54179722HCID 54179722, compoundHCID 178509267HCID 178509267, compound

Product 1

HCID 13476007N-[3-(3-Benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.87 g of 3-amino-4-benzoylpyrazole and 2.46 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]propanamide (Example 169) in 50 ml of glacial acetic acid was refluxed for 15 hours and then evaporated to yield a pale yellow gum. This material was partitioned between an aqueous saturated sodium bicarbonate solution and methylene chloride. The methylene chloride solution was dried with powdered anhydrous sodium sulfate and then passed through a short column of hydrous magnesium silicate adsorbent. The eluate was refluxed in a steam bath and hexane gradually added until turbidity. After cooling, the desired product was recovered by filtration (2.39 g, mp 172°-174° C.).

Workup

  1. customevaporated
  2. customto yield a pale yellow gum
  3. customThis material was partitioned between an aqueous saturated sodium bicarbonate solution and methylene chloride
  4. dry with materialThe methylene chloride solution was dried with powdered anhydrous sodium sulfate
  5. temperatureThe eluate was refluxed in a steam bath
  6. additionhexane gradually added until turbidity
  7. temperatureAfter cooling
  8. filtrationthe desired product was recovered by filtration (2.39 g, mp 172°-174° C.)

Sources & evidence

ORD record
ord-50461ea3038344b3a1dcd9f157bc65a3
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

Loading…