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tert-butyl 3-(5-amino-3-cyclopropyl-1H-pyrazol-1-yl)azetidine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
2.67 g
In ethanol;Reflux;
Example 112 Synthesis of tert-butyl 3-(5-amino-3-cyclopropyl-1H-pyrazol-1-yl)azetidine-1-carboxylate (CF178) 3-Cyclopropyl-3-oxopropanenitrile (2.16 g, 20 mmol) and 1-Boc-3-hydrazinylazetidine- (3.83 g, 20.0 mmol, prepared according to WO 2012/004706 A2) were mixed in ethanol, and the mixture was heated at reflux for overnight. The reaction mixture was cooled to room temperature and ethanol was removed on a rotary evaporator. Water was added and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated on a rotary evaporator. The remaining residue was washed with dichloromethane and filtered to yield CF178 in 2.67 g. 1H NMR (300 MHz, CDCl3): 5.21 (s, 1H), 4.95-4.80 (m, 1H), 4.50-4.35 (m, 2H), 4.30-4.15 (m, 2H), 1.90-1.80 (m, 1H), 1.45 (s, 9H), 0.95-0.80 (m, 2H), 0.70-0.60 (m, 2H). ESI-MS calculated for C1-4H23N4O2 [M+H]+=279.18; Observed: 279.58.
tert-butyl 3-(3-cyclopropyl-5-((7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)amino)-1H-pyrazol-1-yl)azetidine-1-carboxylate[ No CAS ]
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