Pyridine → HCID 56956241, compound

HRID 1036893Notes

Reaction equation

HRID 1036893 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]#[N:21])[CH:14]=2)[NH:9]1.N1C=CC=CC=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl.O>[C:20]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:17][C:16]2([CH3:18])[CH3:19])#[N:21]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67290159HCID 67290159, compound

Product 1

HCID 56956241HCID 56956241, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-aminophenyl)-4,4-dimethyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile (100 mg, 0.36 mmol) and pyridine (0.12 mL, 1.44 mmol) in anhydrous dichloromethane was added methanesulfonyl chloride (41.3 mg, 0.36 mmol) at ice-bath. After addition, the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water, and extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate, concentrated. The residue was purified by prepared HPLC to give N-[2-(6-cyano-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-methanesulfonamide as white solid. LC/MS m/e obsd. (ESI+) [(M+H)+] 356.20.

Workup

  1. additionAfter addition
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customby prepared HPLC

Sources & evidence

ORD record
ord-9b320f48bba5498d8d7b4efb19a695c0
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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