Pyridine → HCID 56966718, compound

HRID 1036879Notes

Reaction equation

HRID 1036879 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14])[CH2:6][C:5]2([CH3:20])[CH3:19].N1C=CC=CC=1.[F:27][C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH:14][S:34]([C:30]1[CH:31]=[CH:32][CH:33]=[C:28]([F:27])[CH:29]=1)(=[O:36])=[O:35])[CH2:6][C:5]2([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 67290769HCID 67290769, compound

Product 1

HCID 56966718HCID 56966718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)aniline (100 mg, 0.35 mmol) in dichloromethane (5 mL) was added pyridine (0.6 mL) and 3-fluorobenzenesulfonyl chloride (68 mg, 0.35 mmol) at ice-bath. The reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with water. The aqueous layer was extracted with dichloromethane. The combined organic layer was washed by brine, dried over anhydrous sodium sulfate, concentrated in vacuo. The residue was purified by HPLC to give N-[2-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-3-fluoro-benzenesulfonamide. LC/MS m/e obsd. (ESI−) [(M−H)−] 443.2.

Workup

  1. washThe reaction mixture was washed with water
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layer was washed by brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-5d181c61d8504a75ab33edfd1aef85fa
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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