Pyridine → HCID 56966357, compound

HRID 1036968Notes

Reaction equation

HRID 1036968 reaction equation
[CH3:1][CH:2]([S:4](Cl)(=[O:6])=[O:5])[CH3:3].[NH2:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:24][C:23]([CH3:26])([CH3:25])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:27]#[N:28])[CH:21]=3)[NH:16]2)[CH:12]=[CH:13][CH:14]=1.N1C=CC=CC=1>ClCCl>[C:27]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]([C:11]1[CH:10]=[C:9]([NH:8][S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5])[CH:14]=[CH:13][CH:12]=1)[CH2:24][C:23]2([CH3:26])[CH3:25])#[N:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 824082-Propanesulfonyl chlorideHCID 67289758HCID 67289758, compound

Product 1

HCID 56966357HCID 56966357, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Propane-2-sulfonyl chloride (231 mg, 1.62 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 (342 mg, 4.32 mmol) in dichloromethane (5 mL). The resultant mixture was allowed to stir for 7 days. 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 propane-2-sulfonic acid [3-(6-cyano-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide as off-white solid (97 mg, yield: 46.8%). MS (ESI+APCI) M+1=384.2.

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-edf9c19cf5ec47a18858283e2d71d79d
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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