HCID 53768224, compound → HCID 21332197, compound

HRID 1390953Notes

Reaction equation

HRID 1390953 reaction equation
[CH2:1]([CH:3]([CH3:31])[C:4]([NH:6][C:7]1[C:8]2[S:15][C:14]3[CH:16]=[C:17]([NH:20]C(OCC4C=CC=CC=4)=O)[CH:18]=[CH:19][C:13]=3[C:9]=2[N:10]([CH3:12])[N:11]=1)=[O:5])[CH3:2]>Br.C(O)(=O)C.CCOCC>[CH2:1]([CH:3]([CH3:31])[C:4]([NH:6][C:7]1[C:8]2[S:15][C:14]3[CH:16]=[C:17]([NH2:20])[CH:18]=[CH:19][C:13]=3[C:9]=2[N:10]([CH3:12])[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 53768224HCID 53768224, compound

Product 1

HCID 21332197HCID 21332197, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of this crude amide in 200 ml of 48% hydrobromic acid in acetic acid was stirred at room temperature for several hours until it was all dissolved. The reaction mixture was then diluted with ether and the solid precipitate that formed was collected by filtration. The solid was distributed between methylene chloride and 10% sodium bicarbonate solution and the organic layer was separated and dried over potassium carbonate. The residue obtained after removal of the solvent in vacuo was chromatographed on silica gel, using toluene/ethyl acetate as solvents, to yield a crystalline product. Recrystallization of this product from nitromethane gave 2-ethyl-N-(6-amino-1-methyl-1H-(1)benzothieno[3,2-c]-pyrazol-3-yl)propanamide, m.p. 196°-197° C.

Workup

  1. customthe solid precipitate that formed
  2. filtrationwas collected by filtration
  3. customthe organic layer was separated
  4. dry with materialdried over potassium carbonate
  5. customThe residue obtained
  6. customafter removal of the solvent in vacuo
  7. customwas chromatographed on silica gel
  8. customto yield a crystalline product
  9. customRecrystallization of this product from nitromethane

Sources & evidence

ORD record
ord-66457ae7d15446428ee578610594f1ae
Source dataset
uspto-grants-1979_02
Patent number
US04140785

Reaction notes

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