Pyridine → HCID 56966278, compound

HRID 1036959Notes

Reaction equation

HRID 1036959 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[CH3:11][C:12]1([CH3:30])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH3:22])[CH:20]=2)[NH:15][CH:14]([C:23]2[CH:24]=[C:25]([NH2:29])[CH:26]=[CH:27][CH:28]=2)[CH2:13]1.N1C=CC=CC=1>ClCCl>[CH3:11][C:12]1([CH3:30])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH3:22])[CH:20]=2)[NH:15][CH:14]([C:23]2[CH:24]=[C:25]([NH:29][S:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)(=[O:9])=[O:8])[CH:26]=[CH:27][CH:28]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 672908283-(4,4,6-Trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

Product 1

HCID 56966278HCID 56966278, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine-3-sulfonyl chloride (96 mg, 0.54 mmol) was added dropwise a mixture of 3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (120 mg, 0.45 mmol) and pyridine (60 mg, 0.76 mmol) in dichloromethane (5 mL). The resultant mixture was allowed to stir overnight. The reaction mixture was washed by water, dried over magnesium sulfate. The mixture was filtered and concentrated to provide the crude product. It was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=4:1) to afford pyridine-3-sulfonic acid [3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide as off-white solid (25 mg, yield: 13.7%). MS (ESI+APCI) M+1=408.2.

Workup

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

Sources & evidence

ORD record
ord-5fcf1949499c4cee9a79c4c02e82774d
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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