Methanol → HCID 178460001, compound

HRID 1282024Notes

Reaction equation

HRID 1282024 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:32])[C:15]([NH:17][C:18]2[N:22](C(OCCCl)=O)[N:21]=[C:20]([CH:29]3[CH2:31][CH2:30]3)[CH:19]=2)=[O:16])=[CH:10][CH:9]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].CO>CN(C)C=O>[CH:29]1([C:20]2[CH:19]=[C:18]([NH:17][C:15](=[O:16])[CH:14]([C:11]3[CH:10]=[CH:9][C:8]([N:7]4[CH2:2][CH2:3][O:4][C:5]4=[O:6])=[CH:13][CH:12]=3)[CH3:32])[NH:22][N:21]=2)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 120438162-Chloroethyl 5-{[2-(4-{[(2-chloroethoxy)carbonyl]amino}phenyl)propanoyl]amino}-3-cyclopropyl-1H-pyrazole-1-carboxylate

Product 1

HCID 178460001HCID 178460001, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

431 mg (0.89 mmol) of 2-chloroethyl 5-{[2-(4-{[(2-chloroethoxy)carbonyl]amino}phenyl)propanoyl]amino}-3cyclopropyl-1H-pyrazole-1-carboxylate were dissolved in 3 ml of N,N-dimethylformamide and 124 mg (0.89 mmol) of potassium carbonate were added and the mixture stirred at room temperature for 19 hours. The reaction mixture was poured into 30 ml of methanol and stirred for 40 minutes, evaporated under vacuum, diluted with 40 ml of methanol and washed with a saturated aqueous ammonium chloride solution. The organic layer was further extracted with dichloromethane, dried over sodium sulfate and evaporated to dryness. The crude was purified by chromatography on a silica gel column to afford 233 mg (77% yield) of the title compound. Analogously, but employing the suitable bisacylated amide derivatives, the following compounds can be prepared:

Workup

  1. stirringstirred for 40 minutes
  2. customevaporated under vacuum
  3. additiondiluted with 40 ml of methanol
  4. washwashed with a saturated aqueous ammonium chloride solution
  5. extractionThe organic layer was further extracted with dichloromethane
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe crude was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-944c85e406084546840515f678114c45
Source dataset
uspto-grants-2002_09
Patent number
US06455559B1

Reaction notes

Loading…