methyl 9-(2-aminoethyl)-2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate → 2-(2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethanamine

HRID 887798Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH:4]1[C:8]2[C:9]3[N:10]([N:13]=[C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:15]=3C(OC)=O)[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5]1>S(=O)(=O)(O)O.O.C(=O)([O-])O.[Na+]>[C:20]1([C:14]2[CH:15]=[C:9]3[C:8]4[CH:4]([CH2:3][CH2:2][NH2:1])[CH2:5][CH2:6][C:7]=4[CH:12]=[CH:11][N:10]3[N:13]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 9-(2-aminoethyl)-2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate (295 mg, 0.881 mmol) was dissolved in 40% (v/v) sulfuric acid (6 mL), and the mixture was stirred at 100° C. for 3 days. The reaction solution was diluted with water and neutralized with sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound. The obtained title compound was used for the reaction of Example 34 without purification.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-284fe1f9459b4f649da7ac3fddf3b845
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247429B2

Reaction notes

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