Pyridine → HCID 56966208, compound

HRID 1036957Notes

Reaction equation

HRID 1036957 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=2)[CH2:3]1.N1C=CC=CC=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:14]=[C:15]([NH:19][S:28]([CH3:27])(=[O:30])=[O:29])[CH:16]=[CH:17][CH:18]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 672908283-(4,4,6-Trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

Product 1

HCID 56966208HCID 56966208, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred mixture of 3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (150 mg, 0.56 mmol) in dichloromethane (3 mL) was added pyridine (79 mg, 1.01 mmol) in dichloromethane (2 mL) and methanesulfonyl chloride (96 mg, 0.84 mmol) under nitrogen. The resultant mixture was stirred for 16 h. The reaction mixture was diluted with dichloromethane, washed with water (twice), saturated brine, and dried over magnesium sulfate. Magnesium sulfate was removed by filtration, and after evaporation, the residue was purified on chromatography column (silica gel, petroleum ether: ethyl acetate=10:1) to afford 63 mg of N-[3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-methanesulfonamide as yellow solid (Yield: 33%). MS (ESI+APCI) M+1=345.2.

Workup

  1. washwashed with water (twice), saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customMagnesium sulfate was removed by filtration
  4. customafter evaporation
  5. customthe residue was purified on chromatography column (silica gel, petroleum ether: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-ba69d5a503794318958fd76088a7ea87
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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