N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamide → N-Desesethylzaleplon

HRID 231505Notes

Reaction equation

HRID 231505 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][NH:4][N:3]=1.CN(C)[CH:11]=[CH:12][C:13]([C:15]1[CH:16]=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:18]=[CH:19][CH:20]=1)=O>C(O)(=O)C>[C:7]([C:6]1[CH:5]=[N:4][N:3]2[C:13]([C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:18]=[CH:19][CH:20]=3)=[CH:12][CH:11]=[N:1][C:2]=12)#[N:8]

Participants

4

Reactant 2

HCID 53412415N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamideHCID 178510443HCID 178510443, compound

Product 1

HCID 9993635N-Desesethylzaleplon

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6.0 g of 3-aminopyrazole-4-carbonitrile, 13.0 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]acetamide and 100 ml of glacial acetic acid was heated at reflux for 4 hours. On standing at room temperature a precipitate formed. The precipitate was isolated, washed with hexane, then ether and dried. The solid was recrystallized from acetonitrile-N,N-dimethylformamide and gave the product of the example, mp 252°-254° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customOn standing at room temperature
  4. customformed
  5. customThe precipitate was isolated
  6. washwashed with hexane
  7. dry with materialether and dried
  8. customThe solid was recrystallized from acetonitrile-N,N-dimethylformamide
  9. customgave the product of the example, mp 252°-254° C.

Sources & evidence

ORD record
ord-c78986580ad74f88be26288bdebc63c9
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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