Hydrochloric Acid → HCID 69331863, compound

HRID 915075Notes

Reaction equation

HRID 915075 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:5]=[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]([C:14]2[CH:15]=[CH:16][C:17](=[O:23])[N:18]([CH:20]([CH3:22])[CH3:21])[N:19]=2)=[N:8][C:9]=1S(C)(=O)=O.Cl.[CH3:31][CH:32]([OH:34])[CH3:33]>>[NH2:3][C:4]1[N:5]=[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]([C:14]2[CH:15]=[CH:16][C:17](=[O:23])[N:18]([CH:20]([CH3:22])[CH3:21])[N:19]=2)=[N:8][C:9]=1[O:34][CH:32]([CH3:33])[CH3:31]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 69331470HCID 69331470, compound

Product 1

HCID 69331863HCID 69331863, compound

Conditions

Temperature
27.5 °C

Procedure

In a sealed tube, NaH (60% in oil suspension) (31.1 mg) was added 2-propanol (0.6 ml) and the mixture was stirred at 25-30° C. for 30 minutes. 6-[5-Amino-6-(methylsulfonyl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (150 mg) was added and the mixture was heated at 100-105° C. for 15 hours. After addition of 0.1N HCl (3 ml) was added to the mixture and an aqueous layer was removed by decantation to give a residue. The residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (70:30 v/v) to give a solid. The solid was crystallized from a mixture of acetone and n-hexane to give 6-(5-amino-6-isopropoxy-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (102 mg).

Workup

  1. temperaturethe mixture was heated at 100-105° C. for 15 hours
  2. additionwas added to the mixture
  3. customan aqueous layer was removed by decantation
  4. customto give a residue
  5. customThe residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (70:30 v/v)
  6. customto give a solid
  7. customThe solid was crystallized from a mixture of acetone and n-hexane

Sources & evidence

ORD record
ord-b9711d0f10ad4df3938b365eca1f008f
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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