Aluminium lithium hydride → HCID 67335147, compound

HRID 1672157Notes

Reaction equation

HRID 1672157 reaction equation
[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]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67336325HCID 67336325, compound

Product 1

HCID 67335147HCID 67335147, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To 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.

Workup

  1. temperatureAfter 2 hours the reaction mixture was cooled
  2. customquenched by the addition of sodium sulfate decahydrate (3 g)
  3. additionThe reaction mixture was diluted with DCM:MeOH:NH4OH (90:9:1, 200 mL)
  4. filtrationthen filtered
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (silica, 3 to 20% of a 9:1 MeOH:NH4OH solution in DCM)

Sources & evidence

ORD record
ord-9a08f65eeb664d419e1cf3a00c399db4
Source dataset
uspto-grants-2011_08
Patent number
US07998963B2

Reaction notes

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