Sodium Hydroxide → HCID 58495469, compound

HRID 1191015Notes

Reaction equation

HRID 1191015 reaction equation
B.CSC.[C:5]([O:9][C:10]([N:12]([CH2:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)[CH:13]([CH3:15])[CH3:14])=[O:11])([CH3:8])([CH3:7])[CH3:6].OS([O-])(=O)=O.[K+].[OH-].[Na+]>C1COCC1.CO>[C:5]([O:9][C:10]([N:12]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[CH:23][CH:24]=1)[CH:13]([CH3:15])[CH3:14])=[O:11])([CH3:7])([CH3:8])[CH3:6]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 12423031(Dimethyl sulfide)trihydroboronHCID 58495527HCID 58495527, compound

Product 1

HCID 58495469HCID 58495469, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere add borane-dimethylsulfide complex (13.7 mL, 27.4 mmol, 2M solution in THF) to 4-[N-(tert-butoxycarbonyl)-N-(iso-propyl)-aminomethyl]-benzonitrile (1.5 g, 5.5 mmol) in THF (20 mL) at 0° C. Warm to room temperature and stir overnight. Heat the mixture under reflux for 2 h. Cool the mixture in an ice-bath and add methanol (20 mL). Warm to room temperature and add KHSO4 (7 g in 50 mL of water). Stir for 2 h at room temperature and basify with 3N aqueous NaOH. Extract with DCM, dry the organic phase over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel (150 g) eluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the title compound as an oil (1.3 g, 85%). MS (APCI+) m/z: 279 (M+H)+.

Workup

  1. temperatureHeat the mixture
  2. temperatureunder reflux for 2 h
  3. temperatureCool the mixture in an ice-bath
  4. temperatureWarm to room temperature
  5. stirringStir for 2 h at room temperature
  6. extractionExtract with DCM
  7. dry with materialdry the organic phase over Na2SO4
  8. concentrationconcentrate in vacuo
  9. customPurify by chromatography on silica gel (150 g)
  10. washeluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-0d08d021c9f24b5a89ccc23aa7ad9aff
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…