Formic Acid → HCID 22629175, compound

HRID 276958Notes

Reaction equation

HRID 276958 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH2:13][CH2:12][N:11]([C:14]([CH2:16][C:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=3[N:23]3[C:28](=[O:29])[CH:27]=[CH:26][C:25]([C:30]4[C:31]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)=[N:32][N:33]5[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=45)=[N:24]3)=[O:15])[CH2:10][CH2:9]2)C=CC=CC=1.C(O)=O.Cl.C(OCC)(=O)C>O>[N:11]1([C:14]([CH2:16][C:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=2[N:23]2[C:28](=[O:29])[CH:27]=[CH:26][C:25]([C:30]3[C:31]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)=[N:32][N:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=34)=[N:24]2)=[O:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 22629172HCID 22629172, compound

Product 1

HCID 22629175HCID 22629175, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 3-[2-{2-(4-triphenylmethylpiperazin-1-ylcarbonyl)methyl-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (4.2 g), formic acid (10 ml) and concentrated hydrochloric acid (1.43 ml) was stirred for 2 hours at room temperature. The reaction mixture was poured into a mixture of ethyl acetate (200 ml) and water (100 ml). Aqueous layer was separated, and the pH was adjusted to pH 12.0 with 4N-aqueous sodium hydroxide solution, which was extracted with dichloromethane (300 ml and 150 ml). Organic phase was combined and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel eluting in turn with 5% and 10% methanol in dichloromethane. Fractions containing desired product were collected, and solvent was removed under reduced pressure to give solid, which was recrystallized from ethyl acetate to give 3-[2-{2-(piperazin-1-ylcarbonyl)methyl-1-cyclohexenyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (2.2 g).

Workup

  1. customAqueous layer was separated
  2. extractionwas extracted with dichloromethane (300 ml and 150 ml)
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave a residue, which
  6. customwas chromatographed on silica gel eluting in turn with 5% and 10% methanol in dichloromethane
  7. additionFractions containing desired product
  8. customwere collected
  9. customsolvent was removed under reduced pressure
  10. customto give solid, which
  11. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-60b4a01e9bca4c79bed31e6325316a94
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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