Pyridine → HCID 56966785, compound

HRID 1036881Notes

Reaction equation

HRID 1036881 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.[CH2:27]([S:29](Cl)(=[O:31])=[O:30])[CH3:28]>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:29]([CH2:27][CH3:28])(=[O:31])=[O:30])[CH2:6][C:5]2([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 67290769HCID 67290769, compound

Product 1

HCID 56966785HCID 56966785, 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 ethanesulfonyl chloride (45 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 ethanesulfonic acid [2-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide LC/MS m/e obsd. (ESI+) [(M+H)+] 379.20.

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-b5a042b5c05d432f9efeaeccf7ce805e
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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