Methanesulfonic Acid → HCID 178437833, compound

HRID 619178Notes

Reaction equation

HRID 619178 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:17]1[CH2:21][CH2:20][C:19]2[CH:22]=[C:23]([CH:26]=O)[CH:24]=[CH:25][C:18]1=2.CS(O)(=O)=O>CCOCC>[CH:1]1([N:6]2[C:10]3=[N:11][C:26]([C:23]4[CH:24]=[CH:25][C:18]5[O:17][CH2:21][CH2:20][C:19]=5[CH:22]=4)=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 7359012,3-Dihydrobenzofuran-5-carboxaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437833HCID 178437833, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.0 g, 9.0 mmol), 2,3-dihydrobenzo[b]furan-5-carboxaldehyde (1.73 g, 11.7 mmol), methanesulfonic acid (0.25 ml) and xylenes (50 ml) was refluxed for 20 hours and then allowed to stand for about 2 days. The reaction mixture was diluted with ether and the product was collected by filtration and dried to afford 1.65 g (52%) of 1-cyclopentyl-3-ethyl-6-(2,3-dihydrobenzo[b]furan-5-yl)pyrazolo[3,4-d]pyrimidin-4-one 1/10 hydrate, m.p. 253-254° C.

Workup

  1. temperaturewas refluxed for 20 hours
  2. filtrationthe product was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-c0bcbf2a7fb44dac81bc733b64d751e7
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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