Hydrochloric Acid → HCID 69331934, compound

HRID 915061Notes

Reaction equation

HRID 915061 reaction equation
[BH4-].[Na+].[I-].[NH2:4][C:5]1[C:6]([C:27]2[CH:32]=[CH:31][N+:30]([CH3:33])=[CH:29][CH:28]=2)=[N:7][C:8]([C:17]2[CH:22]=[CH:21][C:20](=[O:23])[N:19]([CH:24]([CH3:26])[CH3:25])[N:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1.Cl>CO.C(Cl)(Cl)Cl.CC(C)=O>[NH2:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]([C:17]2[CH:22]=[CH:21][C:20](=[O:23])[N:19]([CH:24]([CH3:26])[CH3:25])[N:18]=2)=[N:7][C:6]=1[C:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH:28]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 69332646HCID 69332646, compound

Product 1

HCID 69331934HCID 69331934, compoundYield 13.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

Under ice-cooling, sodium borohydride (30.7 mg) was added to a solution of 4-[3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinyl]-1-methylpyridinium iodide (142 mg) in MeOH (4.26 ml) and the mixture was stirred at the same temperature for 30 minutes. After addition of 1N HCl (0.6 ml), MeOH was evaporated under reduced pressure to give a residue. The residue was dissolved in CHCl3, dried over MgSO4 and purified by column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (5:95 v/v) to give a solid. The solid was suspended in acetone and collected by filtration to give 6-[5-amino-6-(1-methyl-1,2,3,6-tetrahydro-4-pyridyl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (15 mg).

Workup

  1. temperatureUnder ice-cooling
  2. customwas evaporated under reduced pressure
  3. customto give a residue
  4. dry with materialdried over MgSO4
  5. custompurified by column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (5:95 v/v)
  6. customto give a solid
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-fe7082de7ac14650ba492df859c8db3f
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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