Acetic Acid → HCID 24993176, compound

HRID 2042591Notes

Reaction equation

HRID 2042591 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH2:22][CH2:23][C:24](=[O:27])[NH:25][N:26]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1.C(O)(=O)C.[C:32]1(=O)[CH2:35][CH2:34][CH2:33]1.C([BH3-])#N.[Na+]>CN(C=O)C.CO>[CH:32]1([N:8]2[CH2:9][CH2:10][CH:11]([O:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]4[CH2:22][CH2:23][C:24](=[O:27])[NH:25][N:26]=4)=[CH:19][CH:20]=3)[CH2:12][CH2:13]2)[CH2:35][CH2:34][CH2:33]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 5003444Sodium cyanoborohydrideHCID 67010797HCID 67010797, compound

Product 1

HCID 24993176HCID 24993176, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 6-[4-(piperidin-4-yloxy)-phenyl]-4,5-dihydro-2H-pyridazin-3-one trifluoroacetate (6.50 g, 23.8 mmol) in DMF (10 mL), methanol (50 mL), and acetic acid (2 mL) was added cyclobutanone (5.33 mL, 71.3 mmol) and sodium cyanoborohydride (7.47 g, 119 mmol) in portions. After stirring at 60° C. for 4 h, the reaction was concentrated, diluted with dichloromethane, washed with water/brine, dried over sodium sulfate, and concentrated. The product was purified using a Single Step column (9:1 dichloromethane:methanol) and recrystallized from chloroform/ether to obtain 2.2 g (40%); Mp=196-198° C.; MS m/z 328 (M+H).

Workup

  1. concentrationthe reaction was concentrated
  2. additiondiluted with dichloromethane
  3. washwashed with water/brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified
  7. customrecrystallized from chloroform/ether
  8. customto obtain 2.2 g (40%)

Sources & evidence

ORD record
ord-27b35de9185b49d8afa729db818e5f21
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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