Hydrochloric Acid → HCID 16228062, compound

HRID 1191017Notes

Reaction equation

HRID 1191017 reaction equation
CSC.B.[CH3:5][N:6]([CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[CH:7]([CH3:9])[CH3:8].CO.Cl>C1COCC1>[CH3:5][N:6]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH2:16])=[CH:17][CH:18]=1)[CH:7]([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 24696530HCID 24696530, compound

Product 1

HCID 16228062HCID 16228062, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, add borane-dimethyl sulfide complex (8.7 mL, 17.4 mmol, 2M solution in THF) to a solution of 4-[(N-methyl-iso-propylamino)-methyl]-benzonitrile (660 mg, 3.51 mmol) in THF (20 mL) at room temperature then heat to reflux for 30 min. Cool the mixture in an ice-bath and carefully add methanol (10 mL). Warm the mixture to room temperature and add concentrated HCl (10 mL). Stir the mixture for 12 h, and concentrate in vacuo. Purify by chromatography on silica gel (25 g) eluting with a gradient of DCM to 1:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the title compound (550 mg, 82%). MS (ES+) m/z: 193 (M+H)+.

Workup

  1. temperaturethen heat
  2. temperatureto reflux for 30 min
  3. temperatureCool the mixture in an ice-bath
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel (25 g)
  6. washeluting with a gradient of DCM to 1:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-8bcadc8cfec54286b081f8418e61a497
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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