Pyridine → HCID 56966282, compound

HRID 1036965Notes

Reaction equation

HRID 1036965 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:13]=[C:14]([CH:18]2[CH2:27][C:26]([CH3:29])([CH3:28])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:30]#[N:31])[CH:24]=3)[NH:19]2)[CH:15]=[CH:16][CH:17]=1.N1C=CC=CC=1>ClCCl>[C:30]([C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]([C:14]1[CH:13]=[C:12]([NH:11][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH:17]=[CH:16][CH:15]=1)[CH2:27][C:26]2([CH3:29])[CH3:28])#[N:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 67289758HCID 67289758, compound

Product 1

HCID 56966282HCID 56966282, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask, benzenesulfonyl chloride (83 mg, 0.54 mmol) was added dropwise a mixture of 2-(3-amino-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (100 mg, 0.36 mmol) and pyridine (45 mg, 0.54 mmol) in dichloromethane (5 mL). The resultant mixture was allowed to stir overnight. The reaction mixture was washed by water, dried over magnesium sulfate. 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]-benzenesulfonamide as off-white solid (70 mg, yield: 46.5%). MS (ESI+APCI) M+1=418.2.

Workup

  1. washThe reaction mixture was washed by water
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltered
  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-93cd7be495b74130a6259077bf408ec9
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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