Hydrochloric Acid → HCID 68289685, compound

HRID 878755Notes

Reaction equation

HRID 878755 reaction equation
C([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([C:26]2[N:27]=[CH:28][C:29]3[C:34]([C:35]=2[CH3:36])=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=O)C.C[Mg]Br.Cl>C(OCC)C>[OH:21][C:18]([C:8]1[CH:9]=[CH:4][CH:5]=[CH:6][C:7]=1[S:10]([N:13]([C:26]1[N:27]=[CH:28][C:29]2[C:34]([C:35]=1[CH3:36])=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:25])[F:24])=[CH:17][CH:16]=1)(=[O:12])=[O:11])([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68289647HCID 68289647, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68289685HCID 68289685, compoundYield 164.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-acetyl-N-(4-methylisoquinolin-3-yl)-N-[4-(trifluoromethoxy)benzyl]benzenesulfonamide (98 mg, 0.190 mmol) prepared in Example 152 in diethyl ether (2 mL) was added methylmagnesium bromide (tetrahydrofuran solution, 3 mol/L, 0.229 mmol) at 0° C., and the mixture was stirred at room temperature overnight. To the reaction solution was added 1 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→40:60) to give (1-hydroxy-1-methylethyl)-N-(4-methylisoquinolin-3-yl)-N-[4-(trifluoromethoxy)benzyl]benzenesulfonamide (83 mg, 82%) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→40:60)

Sources & evidence

ORD record
ord-dfacf457f6764154993c4eb5c852dad0
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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