Hydrochloric Acid → HCID 57642061, compound

HRID 1174493Notes

Reaction equation

HRID 1174493 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]([CH3:9])=[C:7]([CH:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[F:22])OCC)[C:6](=[O:23])[NH:5]1)[CH3:3].CO.Cl.[H][H]>[Pd].C1COCC1.O>[CH3:3][CH:2]([N:4]1[C:8]([CH3:9])=[C:7]([CH2:10][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[F:22])[C:6](=[O:23])[NH:5]1)[CH3:1]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 57642063HCID 57642063, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 57642061HCID 57642061, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,2-dihydro-1-(1-methylethyl)-4-[(2-fluor-4-methoxyphenyl)-(ethoxy)methyl]-5-methyl-3H-pyrazol-3-one (294 g; 1.28 mol), methanol (4.5 L), aqueous hydrochloric acid (30%; 11 g) and water (80 mL) is hydrogenated with palladium on charcoal (10%-weight) (65 g) at 50° C. and 3 bar hydrogen pressure until hydrogen uptake ceases. THF (2.3 L) is added to the reaction mixture which is then filtered. The catalyst is washed with THF (1 L) and the solvent is distilled off under reduced pressure to a residual volume of approx. 700 to 800 ml. The resulting suspension is poured into water (1 L) with stirring. The precipitate is isolated by filtration, washed with water (400 ml) and dried at 55° C. to yield crystals (light beige).

Workup

  1. filtrationis then filtered
  2. washThe catalyst is washed with THF (1 L)
  3. distillationthe solvent is distilled off under reduced pressure to a residual volume of approx. 700 to 800 ml
  4. additionThe resulting suspension is poured into water (1 L)
  5. customThe precipitate is isolated by filtration
  6. washwashed with water (400 ml)
  7. customdried at 55° C.
  8. customto yield crystals (light beige)

Sources & evidence

ORD record
ord-b2ff115dce764d389747ca75e4230e4d
Source dataset
uspto-grants-2010_11
Patent number
US07838500B2

Reaction notes

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