[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:18][CH2:17][C:11]1([NH:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1To a stirred solution of 1-(1H-indazol-5-ylamino)-cyclohexanecarbonitrile (2.53 g, 10.5 mmol) in THF (40 mL) at room temperature and under nitrogen was added LiAlH4 (21.0 mL of a 1.0 M solution in THF, 21.0 mmol) dropwise over 3 minutes. After 30 minutes the reaction mixture was warmed to 70° C. After 2 hours the reaction mixture was cooled and stirred at ambient temperature for 14 hours, then quenched by the addition of sodium sulfate decahydrate (3 g). The reaction mixture was diluted with DCM:MeOH:NH4OH (90:9:1, 200 mL) then filtered and concentrated in vacuo. Purification by chromatography (silica, 3 to 20% of a 9:1 MeOH:NH4OH solution in DCM) gave (1-aminomethyl-cyclohexyl)-(1H-indazol-5-yl)-amine (0.785 g, 3.22 mmol, 31 %) as a solid.
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