Pyridine → HCID 56967001, compound

HRID 1036912Notes

Reaction equation

HRID 1036912 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.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:28]=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:33]([C:29]1[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=1)(=[O:35])=[O:34])[CH2:6][C:5]2([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 67290769HCID 67290769, compound

Product 1

HCID 56967001HCID 56967001, 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 pyridine-3-sulfonyl chloride (112 mg, 0.35 mmol) at ice-bath. The reaction mixture was stirred at room temperature for 6 h. 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 vacuum. The residue was purified by HPLC to give pyridine-3-sulfonic 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)+] 427.90.

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 vacuum
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-38952eb2a5c94833b7eed46644bbdad5
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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