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

HRID 1088770Notes

Reaction equation

HRID 1088770 reaction equation
C(NC1C=C(C(=O)C=CN(C)C)C=CC=1)(=O)C.NC1C(C#N)=CNN=1.[C:26]([C:28]1[CH:29]=[N:30][N:31]2[C:36]([C:37]3[CH:38]=[C:39]([NH:43][C:44](=[O:46])[CH3:45])[CH:40]=[CH:41][CH:42]=3)=[CH:35][CH:34]=[N:33][C:32]=12)#[N:27].C([BH3-])#N.[Na+]>C(O)(=O)C>[C:26]([C:28]1[CH:29]=[N:30][N:31]2[C:36]([C:37]3[CH:38]=[C:39]([NH:43][C:44](=[O:46])[CH3:45])[CH:40]=[CH:41][CH:42]=3)=[CH:35][CH2:34][NH:33][C:32]=12)#[N:27]

Participants

6

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 9993635N-DesesethylzaleplonHCID 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-e67bc60cd31343499de30b5df7deaa03
Source dataset
uspto-grants-1990_10
Patent number
US04963553

Reaction notes

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