Acetamide → N-[3-(3-cyano-4,5-dihydropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]acetamide

HRID 893649Notes

Reaction equation

HRID 893649 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11](=O)[CH:12]=[CH:13][N:14]([CH3:16])C)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].N[C:19]1[C:23]([C:24]#[N:25])=C[NH:21][N:20]=1.C(N)(=O)C.C([BH3-])#N.[Na+]>C(O)(=O)C>[C:24]([C:23]1[CH:19]=[N:20][N:21]2[C:11]([C:7]3[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][CH:8]=3)=[CH:12][CH2:13][NH:14][C:16]=12)#[N:25]

Participants

6

Reactant 4

HCID 178AcetamideHCID 5003444Sodium cyanoborohydrideHCID 53412415N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamideHCID 178510443HCID 178510443, compound

Product 1

HCID 136093204N-[3-(3-cyano-4,5-dihydropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 7.0 g of 3'-actamido-3-(N,N-dimethylamino)acrylophenone and 3.3 g. of 3-amino-4-cyanopyrazole in 100 ml of acetic acid was heated at reflux for 8 hours. Crystals that formed on cooling were filtered and dried to give 7.4 g. of N-[3-(3-cyano-pyrazolo[1,5-a]pyrimidin-7-yl)phenyl[acetamide, m.p. 254°-256° C. This was reacted with 14.8 g of sodium cyanoborohydride in 50 ml of acetic acid to give 3.0 g of N-[3-(3-cyano-4,5-dihydropyrazolo[1,5-a]pyrimidin-7-yl)phenyl]acetamide, m.p. 251°-254° C. This is reacted with chloroacetic anhydride and sodium carbonate in toluene as in Example 3 to give the title compound.

Workup

  1. temperatureat reflux for 8 hours
  2. customCrystals that formed
  3. temperatureon cooling
  4. filtrationwere filtered
  5. customdried
  6. customto give 7.4 g

Sources & evidence

ORD record
ord-d6be92ae7e474258ba1710bf6b89e926
Source dataset
uspto-grants-1992_06
Patent number
US05126340

Reaction notes

Loading…