HCID 178418361, compound → HCID 178418770, compound

HRID 432765Notes

Reaction equation

HRID 432765 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[N:21]=[C:20]([NH:22][C:23]3[NH:24][N:25]=[C:26]([CH3:28])[CH:27]=3)[C:19]3[C:14](=[CH:15][C:16]([N+:29]([O-])=[O:30])=[CH:17][CH:18]=3)[N:13]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([S:11][C:12]2[N:21]=[C:20]([NH:22][C:23]3[NH:24][N:25]=[C:26]([CH3:28])[CH:27]=3)[C:19]3[C:14](=[CH:15][C:16]([NH:29][OH:30])=[CH:17][CH:18]=3)[N:13]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178418792[2-(4-acetamido-phenylsulfanyl)-7-nitroquinazolin-4-yl] (5-methyl-2H-pyrazol-3-yl)-amine

Product 1

HCID 178418770HCID 178418770, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [2-(4-acetamido-phenylsulfanyl)-7-nitroquinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (147 mg, 3.38.10−4 mol) in methanol (5 mL) is added Pd/C 10% (40 mg) and the reaction mixture is treated with hydrogen at balloon pressure at 45° C. for 20 hours. The catalyst is filtered through a pad of celite which is then washed with dilute HCl. The combined yellow filtrate is evaporated and the resulting solid residue is crystallized from methanol to afford the desired [2-(4-acetamido-phenylsulfanyl)-7-hydroxyaminoquinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine.

Workup

  1. filtrationThe catalyst is filtered through a pad of celite which
  2. washis then washed with dilute HCl
  3. customThe combined yellow filtrate is evaporated
  4. customthe resulting solid residue is crystallized from methanol

Sources & evidence

ORD record
ord-8a48e6a9105c414c8682412feaa72960
Source dataset
uspto-grants-2003_12
Patent number
US06664247B2

Reaction notes

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