Hydrochloric Acid → 2-amino-4,6-dimethyl-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

HRID 1868414Notes

Reaction equation

HRID 1868414 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[S:12]([NH:15][CH:16]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[C:17]([F:20])([F:19])[F:18])(=[O:14])=[O:13].Cl.C(=O)(O)[O-].[Na+]>CO.[Zn]>[NH2:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[S:12]([NH:15][CH:16]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[C:17]([F:20])([F:18])[F:19])(=[O:14])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11697910HCID 11697910, compound

Product 1

HCID 115967172-amino-4,6-dimethyl-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamideYield 86.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 125 mg (0.28 mmol) of 2,4-dimethyl-6-nitro-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide in 5 mL of methanol was added 220 mg (3.36 (mmol) of zinc powder followed by 3 mL of 1 N aqueous HCl. After 3 hours, the mixture was made basic with saturated aqueous sodium bicarbonate solution and extracted with three 10 mL portions of ethyl acetate. The combined organic layers were washed with two 5 mL portions of saturated aqueous sodium bicarbonate solution and three 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The oil residue was chromatographed on silica gel eluting first with dichloromethane-hexanes (1:1) and then ethyl acetate-hexanes (5-20% gradient). The material from the column was solidified from ether-hexanes with a few drops of ethanol to afford 100 mg (85%) of 2-amino-4,6-dimethyl-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide. MS: m/z 412.48 (M+1).

Workup

  1. extractionextracted with three 10 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with two 5 mL portions of saturated aqueous sodium bicarbonate solution and three 5 mL portions of brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe oil residue was chromatographed on silica gel eluting first with dichloromethane-hexanes (1:1)

Sources & evidence

ORD record
ord-f0525e6336274442a003d8c107f08c8b
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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