2-METHYL-2,4,5,6-TETRAHYDROCYCLOPENTA[C]PYRAZOL-3-AMINE synthesis
- Product Name:2-METHYL-2,4,5,6-TETRAHYDROCYCLOPENTA[C]PYRAZOL-3-AMINE
- CAS Number:885529-68-0
- Molecular formula:C7H11N3
- Molecular Weight:137.18
Yield:885529-68-0 52%
Reaction Conditions:
in ethanol at 25 - 80; for 19 h;
Steps:
2-Methyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-amine (63c)
A solution of 2-oxocyclopentanecarbonitrile (63a, 5.21 g, 47.7 mmol) and methyl hydrazine (63b,3.02 mL, 57.3 mmol) in ethanol (200 mL) was stirred initially at room temperature for 1 h. Theresulting mixture was then heated at 80 °C for 18 h, cooled to room temperature and the solventremoved under reduced pressure, and the resulting residue placed under high vacuum overnight.The crude residue was purified by flash column chromatography on silica gel, eluting withmethanol/methylene chloride (gradient of 1:9 to 4:6) to afford 2-methyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-amine (63c) as a yellow solid (3.38 g, 52%): 1H NMR (300 MHz,CDCl3) 3.62 (s, 3H), 3.33 (br s, 2H), 2.65-2.60 (m, 2H), 2.51-2.42 (m, 2H), 2.38-2.30 (m, 2H).
References:
Barnes, Keith D.;Buckle, Ronald N.;Chen, Xinchao;Herr, R. Jason;Johnson, Graham;Lin, Juinn H.;Mayhew, Nicholas J.;Mobley, William C.;Nguyen, Phuong;Paquette, William D.;Rynearson, Kevin D.;Sakwa, Samuel A.;Tanzi, Rudolph E.;Wagner, Steven L.;Yang, Jinhai [Bioorganic and Medicinal Chemistry,2020,vol. 28,# 22,art. no. 115734] Location in patent:supporting information
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