HCID 69934912, compound → HCID 52932687, compound

HRID 536078Notes

Reaction equation

HRID 536078 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:5][C:4]=1[NH:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([N+:25]([O-])=O)[CH:23]=2)[N:18]=[CH:17][N:16]=1>CO.[Pd]>[NH2:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][N:16]=[C:15]2[NH:14][C:4]1[CH:5]=[C:6]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])[CH:7]=[CH:8][C:3]=1[N:2]([CH3:28])[CH3:1]

Participants

4

Reactant 1

HCID 69934912HCID 69934912, compound

Product 1

HCID 52932687HCID 52932687, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(dimethylamino)-N-methyl-3-((6-nitroquinazolin-4-yl)amino)benzene-sulfonamide (715 mg, 1.78 mmol) in MeOH (50 mL) was treated with 10% Pd/C (189 mg, 0.178 mmol) and stirred under H2 (balloon) at 25° C. for 2.5 hours before being filtered through celite and concentrated. The residue was dissolved in CH2Cl2/MeOH, washed with saturated aqueous NaHCO3, dried (Na2SO4), and concentrated to give 3-((6-aminoquinazolin-4-yl)amino)-4-(dimethylamino)-N-methylbenzenesulfonamide (433 mg, 59%) as a yellow solid.

Workup

  1. filtrationbefore being filtered through celite
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2/MeOH
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-832527858b83465a87234436d87771ff
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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