Sodium borohydride → HCID 68183317, compound

HRID 513694Notes

Reaction equation

HRID 513694 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[C:5](/[C:14](=[N:22]/[CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])/[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2>CCO>[NH2:3][C:4]1[C:5]([CH:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[NH:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178483763HCID 178483763, compound

Product 1

HCID 68183317HCID 68183317, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

NaBH4 (181 mg, 4.9 mmol) was added to a solution of N-[1-(8-amino-quinolin-7-yl)-1-(4-fluoro-phenyl)-meth-(E)-ylidene]-N′,N′-dimethyl-ethane-1,2-diamine 414 (550 mg, 1.63 mmol) in EtOH (12 ml) at 0° C. and the mixture was heated at 80° C. for 4 h. After cooling, the reaction was quenched with water and the aqueous phase was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (97:3) to give the title compound (420 mg, 75%).

Workup

  1. temperatureAfter cooling
  2. customthe reaction was quenched with water
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with DCM/MeOH (97:3)

Sources & evidence

ORD record
ord-4f9d47227e254c40ac02b1a720a32962
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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