(4-Amino-3-methylphenyl)methanesulfonamide → 5,9-Bis(2,2,2-trifluoroethoxy)-7-[2-methyl-4-(sulfamoylmethyl)phenyl]-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-6,8-dione

HRID 907471Notes

Reaction equation

HRID 907471 reaction equation
[F:1][C:2]([F:27])([F:26])[CH2:3][O:4][C:5]1[C:14]2[C:15](=O)[O:16][C:17](=[O:18])[C:13]=2[C:12]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][S:36]([NH2:39])(=[O:38])=[O:37])=[CH:31][C:30]=1[CH3:40]>CC(O)=O>[O:16]=[C:15]1[C:14]2[C:5]([O:4][CH2:3][C:2]([F:26])([F:1])[F:27])=[C:6]3[C:11](=[C:12]([O:20][CH2:21][C:22]([F:25])([F:23])[F:24])[C:13]=2[C:17](=[O:18])[N:28]1[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][S:36]([NH2:39])(=[O:37])=[O:38])=[CH:31][C:30]=1[CH3:40])[N:10]=[CH:9][CH:8]=[CH:7]3

Participants

4

Reactant 2

HCID 44244999(4-Amino-3-methylphenyl)methanesulfonamideHCID 442455085,9-Bis(2,2,2-trifluoroethoxy)furo[3,4-g]quinoline-6,8-dione

Product 1

HCID 442453445,9-Bis(2,2,2-trifluoroethoxy)-7-[2-methyl-4-(sulfamoylmethyl)phenyl]-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-6,8-dioneYield 82.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture containing 5,9-bis(2,2,2-trifluoroethoxy)furo[3,4-g]quinoline-6,8-dione (42 g, 106 mmol) 5 and 1-(4-amino-3-methylphenyl)methanesulfonamide 15 (24 g, 1.13 equiv) from Preparative Example 1 in AcOH (350 ml) was degassed under vacuum and heated to reflux under nitrogen for 6.5 h. The solvent was then evaporated and the residue was partially dissolved into 50% EtOAc/toluene (800 ml) and cooled down to 0 C. The solid was filtered and washed with toluene to yield a first crop of material as a brownish solid (50.36 g).

Workup

  1. customwas degassed under vacuum
  2. temperatureheated
  3. temperatureto reflux under nitrogen for 6.5 h
  4. customThe solvent was then evaporated
  5. dissolutionthe residue was partially dissolved into 50% EtOAc/toluene (800 ml)
  6. temperaturecooled down to 0 C
  7. filtrationThe solid was filtered
  8. washwashed with toluene

Sources & evidence

ORD record
ord-6d74bcc1089b4716afa8457f2d749698
Source dataset
uspto-grants-2011_09
Patent number
US08013159B2

Reaction notes

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