6-[4-(2-t-butoxycarbonylamino-2-methylpropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone → 6-[4-(2-amino-2-methylpropyl amino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

HRID 1905416Notes

Reaction equation

HRID 1905416 reaction equation
C(OC([NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]([CH3:25])[CH2:20][C:21](=[O:24])[NH:22][N:23]=2)=[CH:14][CH:13]=1)=O)(C)(C)C.C(OCC)(=O)C.Cl>C(OCC)(=O)C>[NH2:8][C:9]([CH3:26])([CH3:27])[CH2:10][NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:19]([CH3:25])[CH2:20][C:21](=[O:24])[NH:22][N:23]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 108332506-[4-(2-t-butoxycarbonylamino-2-methylpropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinoneHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 106123876-[4-(2-amino-2-methylpropyl amino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinoneYield 75.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The 6-[4-(2-t-butoxycarbonylamino-2-methylpropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (3.74 g) obtained in (1-c) above was dissolved in ethyl acetate (10 ml), and 15% hydrogen chloride-ethyl acetate solution (40 ml) was added. The mixture was stirred for 2 hours, and the solvent was evaporated under reduced pressure. The residue was dissolved in water, made alkaline with sodium carbonate, and extracted with chloroform. The extract was dried over MgSO4, and the solvent was evaporated to give 6-[4-(2-amino-2-methylpropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (2.06 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with chloroform
  4. dry with materialThe extract was dried over MgSO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1da59c6e06b340ceb817b9d8b21d183b
Source dataset
uspto-grants-1989_06
Patent number
US04843072

Reaction notes

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