Cyclopentylamine → HCID 18789034, compound

HRID 1106528Notes

Reaction equation

HRID 1106528 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:3]=1[CH2:16][CH2:17]Cl.[CH:19]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C=O)C>[CH:19]1([N:24]2[C:2]3[N:7]4[N:8]=[CH:9][CH:10]=[C:6]4[N:5]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:3]=3[CH2:16][CH2:17]2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 18789151HCID 18789151, compound

Product 1

HCID 18789034HCID 18789034, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 48 ml of anhydrous DMF were dissolved 3.6 g of ethyl 7-chloro-6-(2-chloroethyl)pyrazolo[1,5-a]pyrimidine-5-carboxylate. While stirring at room temperature under a nitrogen atmosphere, 7.3 ml of cyclopentylamine were added to the solution, and the mixture was stirred for 1 hour and 20 minutes. The reaction mixture was poured into 250 ml of ice water. Insoluble matter was collected by filtration and air-dried to obtain 3.20 g (yield: 85.3%) of ethyl 8-cyclopentyl-6,7-dihydro-8H-pyrrolo[3,2-e]pyrazolo[1,5-a]-pyrimidine-5-carboxylate. While stirring at -5 to 0° C., 1.16 g of this product were gradually added to mixed acid prepared by mixing 7.8 ml of concentrated sulfuric acid and 3.9 ml of 90% nitric acid. After being stirred for 5 minutes under the same conditions, the reaction mixture was poured into 200 ml of ice water, followed by extraction with chloroform. After the chloroform layer was dried over anhydrous sodium sulfate, the solvent was then distilled off, and the residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane=1:1) to obtain 0.76 g (yield: 57.0%) of Compound 21.

Workup

  1. stirringthe mixture was stirred for 1 hour and 20 minutes
  2. filtrationInsoluble matter was collected by filtration
  3. customair-dried

Sources & evidence

ORD record
ord-6b4af0f1ab8e49cab1edf308718f6e44
Source dataset
uspto-grants-2000_05
Patent number
US06057330

Reaction notes

Loading…