Aluminium lithium hydride → HCID 25105787, compound

HRID 1966851Notes

Reaction equation

HRID 1966851 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH:10]1[CH2:37][CH2:36][C:13]2([O:17][N:16]=[C:15]([C:18]3[CH:23]=[N:22][C:21]4[N:24]([CH2:27][CH3:28])[N:25]=[CH:26][C:20]=4[C:19]=3[NH:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:14]2)[CH2:12][CH2:11]1)=[N+]=[N-]>O1CCCC1>[CH:30]1([NH:29][C:19]2[C:18]([C:15]3[CH2:14][C:13]4([CH2:36][CH2:37][CH:10]([NH2:7])[CH2:11][CH2:12]4)[O:17][N:16]=3)=[CH:23][N:22]=[C:21]3[N:24]([CH2:27][CH3:28])[N:25]=[CH:26][C:20]=23)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86647606HCID 86647606, compound

Product 1

HCID 25105787HCID 25105787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (0.0018 mole) is taken in tetrahydrofuran. 5-(8-Azido-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-N-cyclohexyl-1-ethyl-1H-pyrazolo[3,4-b]pyridin-4-amine (0.00047 mole) (example 46) is added. The reaction mixture is stirred at room temperature overnight. It is quenched with aqueous sodium sulphate solution followed by ethyl acetate. The filtration is done through celite pad and extraction is done with ethyl acetate. The organic layer is washed with brine, dried and concentrated under reduced pressure to give crude compound, which is purified by column chromatography.

Workup

  1. customIt is quenched with aqueous sodium sulphate solution
  2. filtrationThe filtration
  3. extractionis done through celite pad and extraction
  4. washThe organic layer is washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto give crude compound, which
  8. customis purified by column chromatography

Sources & evidence

ORD record
ord-db4d90af6ddf4dbe96dd248ce6ee7232
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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