Aluminium lithium hydride → HCID 59436027, compound

HRID 1802471Notes

Reaction equation

HRID 1802471 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]=[C:7]([NH:15][C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:19]#[N:20])[C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:20][CH2:19][C:18]1[CH:21]=[CH:22][C:23]([CH3:24])=[C:16]([NH:15][C:7]2[C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]3[CH:3]=[C:2]([F:1])[CH:26]=[CH:25][C:5]=3[N:6]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59436092HCID 59436092, compound

Product 1

HCID 59436027HCID 59436027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-2,6-naphthyridin-5-yl)amino]-4-methylbenzonitrile (40 mg, 0.12 mmol) in THF (1.1 mL) at 0° C. was added lithium aluminum hydride (0.4 mL, 1 M, 0.40 mmol). The reaction was stirred for 18 hours and then quenched by the addition of 0.02 mL water, then 0.02 mL 10% aq. NaOH and finally 0.05 mL water. The mixture was then poured into a separatory funnel with water and EtOAc. The mixture was extracted with EtOAc and the extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatographpy (0-10% MeOH/CH2Cl2 (with 1% NH4OH)) afforded the title compound.

Workup

  1. customquenched by the addition of 0.02 mL water
  2. additionThe mixture was then poured into a separatory funnel with water and EtOAc
  3. extractionThe mixture was extracted with EtOAc
  4. washthe extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel column chromatographpy (0-10% MeOH/CH2Cl2 (with 1% NH4OH))

Sources & evidence

ORD record
ord-6d2b0c20a73141e685fc2389007599b1
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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