Pyridine → HCID 56966355, compound

HRID 1036966Notes

Reaction equation

HRID 1036966 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]([CH:13]2[CH2:22][C:21]([CH3:24])([CH3:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:25]#[N:26])[CH:19]=3)[NH:14]2)[CH:10]=[CH:11][CH:12]=1.N1C=CC=CC=1>ClCCl>[C:25]([C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]([C:9]1[CH:8]=[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:12]=[CH:11][CH:10]=1)[CH2:22][C:21]2([CH3:24])[CH3:23])#[N:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67289758HCID 67289758, compound

Product 1

HCID 56966355HCID 56966355, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (93 mg, 0.81 mmol) was added dropwise to a mixture of 2-(3-amino-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (150 mg, 0.54 mmol) and pyridine (77 mg, 0.97 mmol) in dichloromethane (5 mL). The resultant mixture was allowed to stir overnight. The reaction mixture was washed by water, dried over magnesium sulfate. It was filtered and concentrated to provide the crude product. It was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=5:1) to afford N-[3-(6-cyano-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-methanesulfonamide as off-white solid (100 mg, Yield: 52.1%). MS (ESI+APCI) M+1=356.2.

Workup

  1. washThe reaction mixture was washed by water
  2. dry with materialdried over magnesium sulfate
  3. filtrationIt was filtered
  4. concentrationconcentrated
  5. customto provide the crude product
  6. customIt was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-25fb32d9045e4310906bf104da6825ec
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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