N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethyl-4-methylbenzenesulfonamide → N-ethyl-N-[3-[3-(2-furanylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-4-methylbenzenesulfonamide

HRID 1247967Notes

Reaction equation

HRID 1247967 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[O:8])=[CH:5][NH:4][N:3]=1.CN(C)[CH:16]=[CH:17][C:18]([C:20]1[CH:21]=[C:22]([N:26]([CH2:37][CH3:38])[S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH:23]=[CH:24][CH:25]=1)=O>C(O)(=O)C>[CH2:37]([N:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:18]2[N:3]3[N:4]=[CH:5][C:6]([C:7]([C:9]4[O:10][CH:11]=[CH:12][CH:13]=4)=[O:8])=[C:2]3[N:1]=[CH:16][CH:17]=2)[CH:21]=1)[S:27]([C:30]1[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=1)(=[O:29])=[O:28])[CH3:38]

Participants

4

Reactant 2

HCID 53660891N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethyl-4-methylbenzenesulfonamideHCID 178509268HCID 178509268, compound

Product 1

HCID 20280467N-ethyl-N-[3-[3-(2-furanylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-4-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5.9 g of (3-amino-1H-pyrazol-4-yl)-2-furanylmethanone, 12.4 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethyl-4-methylbenzenesulfonamide and 200 ml of glacial acetic acid was refluxed for 18 hours, then cooled to room temperature and evaporated to dryness. The residue was partitioned between 200 ml of dichloromethane and 100 ml of saturated aqueous sodium bicarbonate. The dichloromethane layer was dried, then filtered through hydrous magnesium silicate and washed with 200 ml of dichloromethane. The filtrate and wash were combined with 200 ml of hexane, concentrated to 250 ml, diluted with 100 ml of hexane and concentrated to turbidity. A heavy oil formed which was separated and cooled to -10° C. producing a solid. This solid was washed with hexane and then dried in vacuo at 60° C. giving N-ethyl-N-[3-[3-(2-furanylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-4-methylbenzenesulfonamide.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customevaporated to dryness
  3. customThe residue was partitioned between 200 ml of dichloromethane and 100 ml of saturated aqueous sodium bicarbonate
  4. dry with materialThe dichloromethane layer was dried
  5. filtrationfiltered through hydrous magnesium silicate
  6. washwashed with 200 ml of dichloromethane
  7. washThe filtrate and wash
  8. concentrationconcentrated to 250 ml
  9. additiondiluted with 100 ml of hexane
  10. concentrationconcentrated to turbidity
  11. customA heavy oil formed which
  12. customwas separated
  13. temperaturecooled to -10° C.
  14. customproducing a solid
  15. washThis solid was washed with hexane
  16. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-9738eac6ce8d448c8d449f5b17982e73
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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