Pyridine → HCID 56966358, compound

HRID 1036969Notes

Reaction equation

HRID 1036969 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]2[CH2:28][C:27]([CH3:30])([CH3:29])[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:31]#[N:32])[CH:25]=3)[NH:20]2)[CH:16]=[CH:17][CH:18]=1.N1C=CC=CC=1>ClCCl>[C:31]([C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]([C:15]1[CH:14]=[C:13]([NH:12][S:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH:18]=[CH:17][CH:16]=1)[CH2:28][C:27]2([CH3:30])[CH3:29])#[N:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 67289758HCID 67289758, compound

Product 1

HCID 56966358HCID 56966358, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methyl-benzenesulfonyl chloride (103 mg, 0.54 mmol) was added dropwise to 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 (51 mg, 0.65 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]-4-methyl-benzenesulfonamide as off-white solid (60 mg, yield: 38.6%). MS (ESI+APCI) M+1=432.2.

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-13a64db7de724daab82e436212cb38b6
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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