Hydrochloric Acid → 2-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(2-fluorobenzyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097402Notes

Reaction equation

HRID 2097402 reaction equation
C(OC[N:10]1[C:14]2[CH:15]=[N:16][NH:17][C:18](=[O:19])[C:13]=2[C:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])=[C:11]1[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH:35]([F:37])[F:36])=[C:30]([O:38][CH:39]2[CH2:41][CH2:40]2)[CH:29]=1)C1C=CC=CC=1.Cl.[H][H]>[Pd].C(O)C>[CH:39]1([O:38][C:30]2[CH:29]=[C:28]([C:11]3[NH:10][C:14]4[CH:15]=[N:16][NH:17][C:18](=[O:19])[C:13]=4[C:12]=3[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[CH:33]=[CH:32][C:31]=2[O:34][CH:35]([F:37])[F:36])[CH2:41][CH2:40]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66602968HCID 66602968, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1358450372-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(2-fluorobenzyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 330 ml of ethanol solution containing 4.28 g (7.62 mmol) of 1-benzyloxymethyl-2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-(2-fluorobenzyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 22-(a) were added 1.50 g of 5% palladium-active carbon and 3.8 ml of 2N hydrochloric acid, and then the mixture was stirred under 1 atm hydrogen atmosphere at 50° C. for 1 hour. After completion of the reaction, the reaction mixture was filtered, the filtrate was concentrated under reduced pressure, methanol and 28% aqueous ammonia were added to the obtained solid, and the mixture was stirred for 1 hour. Then, the solution was concentrated under reduced pressure, water was added to the obtained concentrate, and the precipitated solid was collected by filtration. The obtained solid was washed with water and dried under reduced pressure to obtain 2.99 g of the title compound as a white solid. (Yield: 89%)

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure, methanol and 28% aqueous ammonia
  4. additionwere added to the obtained solid
  5. concentrationThen, the solution was concentrated under reduced pressure, water
  6. additionwas added to the obtained
  7. concentrationconcentrate
  8. filtrationthe precipitated solid was collected by filtration
  9. washThe obtained solid was washed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-34f654b49c6e42e4964d63aaea75100b
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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