Acetonitrile → HCID 57969561, compound

HRID 1920873Notes

Reaction equation

HRID 1920873 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[C:17]([CH3:18])=[CH:16][N:15]=[C:14]3[NH:19][N:20]=[CH:21][C:13]=23)[CH:7]=1)([CH3:5])[C:3]#[N:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].CC#N>C1COCC1>[CH3:5][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[C:17]([CH3:18])=[CH:16][N:15]=[C:14]3[NH:19][N:20]=[CH:21][C:13]=23)[CH:7]=1)([CH3:1])[CH2:3][NH2:4]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 21226445Aluminium lithium hydrideHCID 57969686HCID 57969686, compound

Product 1

HCID 57969561HCID 57969561, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution of 2-methyl-2-(3-(5-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)propanenitrile (108 mg, 0.3908 mmol) at 0° C. in THF (20 ml) was added slowly a solution of lithium aluminium hydride (781.5 μL of 2 M, 1.563 mmol). The reaction mixture was allowed to stir at 0° C. for 2 hours and then allowed to warm to RT and stirred for 16 hours. The mixture was then cooled to 0° C. and quenched with water. EtOAc was added and the mixture passed through a celite pad. The organics were separated, washed with saturated NaCl, dried over Na2SO4, filtered and concentrated under reduced pressure to give a semi solid which was lyophilized from MeCN/H20 (34 mg, Yield=31%).

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 16 hours
  3. temperatureThe mixture was then cooled to 0° C.
  4. customquenched with water
  5. additionEtOAc was added
  6. customThe organics were separated
  7. washwashed with saturated NaCl
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto give a semi solid which

Sources & evidence

ORD record
ord-4fe115e0ba5e43e89e4d9b17f7760224
Source dataset
uspto-grants-2012_05
Patent number
US08173635B2

Reaction notes

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