[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:10][NH:11][C:12]2[CH:16]=[CH:15][N:14]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[N:13]=2)[CH2:9][CH2:8]1>C1COCC1>[CH:7]1([CH2:10][NH:11][C:12]2[CH:16]=[CH:15][N:14]([C:17]3[CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[CH:23][CH:24]=3)[N:13]=2)[CH2:9][CH2:8]1Add a solution of 1M lithium aluminum hydride in THF (1.4 mL, 1.4 mmol) to a solution of 4-[3-(cyclopropylmethyl-amino)-pyrazol-1-yl]-benzonitrile (136 mg, 0.57 mmol) in THF (10 mL) at room temperature under a nitrogen atmosphere. Stir the mixture for 1 h at 60° C. Cool the mixture to room temperature and quench slowly with water, 1N NaOH and additional water. Dilute with EtOAc, stir vigorously for 20 min and filter through Celite®. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify the residue by SCX chromatography to obtain the desired intermediate that was used without further purification (130 mg, 94%). MS (ES+) m/z: 243 (M+H)+.
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