Hydrochloric Acid → HCID 20725517, compound

HRID 1582319Notes

Reaction equation

HRID 1582319 reaction equation
[OH-:1].[Li+].[F:3][C:4]1[CH:28]=[CH:27][C:7]([CH2:8][O:9][C:10]2[N:11]=[N:12][CH:13]=[C:14]3[C:18]([CH:19]=[O:20])=[C:17]([CH3:21])[N:16]([CH2:22][C@H:23]4[CH2:25][C@@H:24]4[CH3:26])[C:15]=23)=[CH:6][CH:5]=1.Cl>O.C(O)C.[N+]([O-])([O-])=O.[Ag+]>[C:19]([C:18]1[C:14]2[C:15](=[C:10]([O:9][CH2:8][C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:28][CH:27]=3)[N:11]=[N:12][CH:13]=2)[N:16]([CH2:22][C@H:23]2[CH2:25][C@@H:24]2[CH3:26])[C:17]=1[CH3:21])([OH:1])=[O:20]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86590811HCID 86590811, compound

Product 1

HCID 20725517HCID 20725517, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of silver nitrate (0.85 g, 5 mmol) in water (2.5 ml) was added an aqueous 2N lithium hydroxide solution (3 ml), followed by a solution of 7-(4-fluorobenzyloxy)-3-formyl-2-methyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrolo[2,3-d]pyridazine (0.177 g, 0.5 mmol) in ethanol (10 ml). The mixture was stirred at room temperature for 48 hours. To the reaction mixture was added 1N hydrochloric acid (3 ml) and the resulting mixture was filtered through celite (trade mark). The celite (trade mark) was washed with ethanol (30 ml). To the combined filtrates was added water and the resulting mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel column using chloroform/isopropanol=19/1 as the eluant to give the title compound (0.094 g, 51%) as pale yellow crystals.

Workup

  1. filtrationthe resulting mixture was filtered through celite (trade mark)
  2. washThe celite (trade mark) was washed with ethanol (30 ml)
  3. additionTo the combined filtrates was added water
  4. extractionthe resulting mixture was extracted with chloroform
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-c31c3375d0ea4087a160d2da8e2b928e
Source dataset
uspto-grants-2004_05
Patent number
US06734181B2

Reaction notes

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