Methanol → HCID 56839371, compound

HRID 1747803Notes

Reaction equation

HRID 1747803 reaction equation
[Br-].[CH2:2]([N+:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:20]=[CH:19][C:18](=[O:21])[C:17]([C:22]3[N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:25]=[CH:24][CH:23]=3)=[N:16]2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+].[OH2:35].[CH3:36]O>>[CH2:2]([N:9]1[CH2:10][CH:11]=[C:12]([N:15]2[CH:20]=[C:19]([O:35][CH3:36])[C:18](=[O:21])[C:17]([C:22]3[N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:25]=[CH:24][CH:23]=3)=[N:16]2)[CH2:13][CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86723592HCID 86723592, compound

Product 1

HCID 56839371HCID 56839371, compound

Procedure

To a solution of 1-benzyl-4-[4-oxo-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-1(4H)-yl]pyridinium bromide (0.73 g) in methanol (30 mL) was added sodium borohydride (0.21 g) at 0° C., and the mixture was stirred at room temperature overnight. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with ethyl acetate and recrystallized from ethyl acetate to give the title compound (0.15 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe obtained crystals were washed with ethyl acetate
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4ebe336945364131b02ae9311b41c994
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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