Hydrochloric Acid → 6-(6-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

HRID 915040Notes

Reaction equation

HRID 915040 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][CH:14]=[C:13]([NH:23]CC3C=CC(OC)=CC=3)[N:12]=2)=[N:5]1)([CH3:3])[CH3:2].Cl>C1(C)C=CC=CC=1>[NH2:23][C:13]1[N:12]=[C:11]([C:6]2[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 693319672-isopropyl-6-{6-[(4-methoxybenzyl)amino]-3-phenyl-2-pyrazinyl}-3(2H)-pyridazinone

Product 1

HCID 693314606-(6-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinoneYield 47.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2-isopropyl-6-{6-[(4-methoxybenzyl)amino]-3-phenyl-2-pyrazinyl}-3(2H)-pyridazinone (2.01 g) in a mixture of toluene (1 ml) and conc. HCl (6 ml) was refluxed for 4 hours. After cooling, an organic layer was removed and an aqueous layer was adjusted to pH 8 with 8N aq. NaOH to yield a precipitate. The precipitate was collected by filtration and dried under reduced pressure and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (30:70 v/v) to give 6-(6-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone as a solid (680 mg).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureAfter cooling
  3. customan organic layer was removed
  4. customto yield a precipitate
  5. filtrationThe precipitate was collected by filtration
  6. customdried under reduced pressure
  7. custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (30:70 v/v)

Sources & evidence

ORD record
ord-0893b003b90149b287d91dbafb78bba4
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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