O-Phenylenediamine → HCID 11422096, compound

HRID 1455664Notes

Reaction equation

HRID 1455664 reaction equation
Br[CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[CH:22]=[C:23]([C:31]([CH3:37])([S:33]([CH3:36])(=[O:35])=[O:34])[CH3:32])[CH:24]=[C:25]3[C:30]=2[N:29]=[CH:28][CH:27]=[CH:26]3)[CH:16]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[NH2:45]>CN(C=O)C.O>[CH3:37][C:31]([C:23]1[CH:24]=[C:25]2[C:30](=[C:21]([C:17]3[CH:16]=[C:15]([C:2]4[C:3]([C:5]5[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:12])=[O:13])=[CH:7][CH:6]=5)=[N:45][C:40]5[C:39](=[CH:44][CH:43]=[CH:42][CH:41]=5)[N:38]=4)[CH:20]=[CH:19][CH:18]=3)[CH:22]=1)[N:29]=[CH:28][CH:27]=[CH:26]2)([S:33]([CH3:36])(=[O:35])=[O:34])[CH3:32]

Participants

5

Reactant 2

HCID 7243O-PhenylenediamineHCID 86608354HCID 86608354, compound

Product 1

HCID 11422096HCID 11422096, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-2-(3-{6-[1-methyl-1-(methylsulfonyl)ethyl]quinolin-8-yl}phenyl)-1-[4-(methylsulfonyl)phenyl]ethanone from EXAMPLE 1, step 4 in DMF (0.05M) and 1,2-diaminobenzene (2 eq) was stirred at 130° C. for 18 h. The reaction mixture was cooled to rt, diluted with water and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (hexane:EtOAc, 1:1) to afforded the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (hexane:EtOAc, 1:1)

Sources & evidence

ORD record
ord-a9effbf14ea04dbb9c2ce978b574f517
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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