HCID 9906644, compound → HCID 86590811, compound

HRID 1582318Notes

Reaction equation

HRID 1582318 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][O:7][C:8]2[N:9]=[N:10][CH:11]=[C:12]3[C:16]([CH2:17][OH:18])=[C:15]([CH3:19])[N:14]([CH2:20][C@H:21]4[CH2:23][C@@H:22]4[CH3:24])[C:13]=23)=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[N:9]=[N:10][CH:11]=[C:12]3[C:16]([CH:17]=[O:18])=[C:15]([CH3:19])[N:14]([CH2:20][C@H:21]4[CH2:23][C@@H:22]4[CH3:24])[C:13]=23)=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 9906644HCID 9906644, compound

Product 1

HCID 86590811HCID 86590811, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(4-fluorobenzyloxy)-3-hydroxymethyl-2-methyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrolo[2,3-d]pyridazine (64.3 g, 181 mmol) in methylene chloride (900 ml) was added activated manganese dioxide (472 g, 5.43 mol) at room temperature. The mixture was stirred at room temperature for 18 hours. The reaction mixture was filtered through celite (trade mark) and the filtrate was concentrated in vacuo. The crude crystals (45.7 g) were washed with ethyl acetate and hexane to give the title compound (44.3 g, 69%) as pale yellow crystals.

Workup

  1. filtrationThe reaction mixture was filtered through celite (trade mark)
  2. concentrationthe filtrate was concentrated in vacuo
  3. washThe crude crystals (45.7 g) were washed with ethyl acetate and hexane

Sources & evidence

ORD record
ord-9dddbf23d9504892918cf09b7fa4e13d
Source dataset
uspto-grants-2004_05
Patent number
US06734181B2

Reaction notes

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