Methanesulfonyl chloride → HCID 17962880, compound

HRID 557604Notes

Reaction equation

HRID 557604 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[OH:22])=[CH:11][CH:12]=2)[C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([CH3:24])[CH2:6][C:5]1([CH3:32])[CH3:31])(=[O:3])[CH3:2].[CH3:33][S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][S:34]([CH3:33])(=[O:36])=[O:35])=[CH:11][CH:12]=2)[C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([CH3:24])[CH2:6][C:5]1([CH3:32])[CH3:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 17962902HCID 17962902, compound

Product 1

HCID 17962880HCID 17962880, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Sulfonylation of 1-acetyl-6-(2-hydroxybenzoyl)amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (12 mg) with methylsulfonyl chloride (6.5 μl) was performed in pyridine (1 ml). TLC analysis after stirring for 16 h showed conversion to a higher-running product. The mixture was concentrated, the residue was dissolved in dichloromethane and washed with water. The organic layer was dried (Na2SO4) and concentrated in vacuo. The crude product was purified by silica gel column chromatography. Eluent: heptane/ethyl acetate=8/2 (v/v).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d732457a7f624025ba12af0a7ff8b0d8
Source dataset
uspto-grants-2011_11
Patent number
US08058441B2

Reaction notes

Loading…