Acetic Acid → HCID 89586301, compound

HRID 1747805Notes

Reaction equation

HRID 1747805 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[C:17](=[O:18])[CH:16]=[CH:15][N:14]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[N:13]=3)=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][C:26]([CH3:28])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH3:25][CH:26]([N:22]1[CH2:23][CH2:24][CH:19]([N:14]2[CH:15]=[CH:16][C:17](=[O:18])[C:12]([C:11]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[CH:9][CH:10]=3)=[N:13]2)[CH2:20][CH2:21]1)[CH3:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 68014851HCID 68014851, compound

Product 1

HCID 89586301HCID 89586301, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(1-Phenyl-1H-pyrazol-5-yl)-1-piperidin-4-ylpyridazin-4(1H)-one (0.20 g), acetone (0.23 mL) and acetic acid (1.0 mL) were dissolved in THF (10 mL), sodium triacetoxyborohydride (0.66 g) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and neutralized with saturated sodium hydrogen carbonate. Sodium chloride was added to saturation, and the mixture was extracted with ethyl acetate/THF. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, THF) and recrystallized from ethyl acetate/hexane to give the title compound (0.15 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionSodium chloride was added to saturation
  3. extractionthe mixture was extracted with ethyl acetate/THF
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, THF)
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2285c5b096dd46e8a604fbf350cd7ee4
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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