Methanol → HCID 24992520, compound

HRID 2042582Notes

Reaction equation

HRID 2042582 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][C:18](=[O:21])[NH:19][N:20]=3)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.CO.[C:24]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25]1.C([BH3-])#N.[Na+]>CN(C=O)C.C(O)(=O)C>[CH:24]1([N:2]2[CH2:3][CH2:4][CH:5]([O:8][C:9]3[N:14]=[CH:13][C:12]([C:15]4[CH:16]=[CH:17][C:18](=[O:21])[NH:19][N:20]=4)=[CH:11][CH:10]=3)[CH2:6][CH2:7]2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 67011094HCID 67011094, compound

Product 1

HCID 24992520HCID 24992520, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

6-[6-(piperidin-4-yloxy)-pyridin-3-yl]-2H-pyridazin-3-one hydrochloride (407 mg, 1.18 mmol) in a mixture of DMF (5 mL), methanol (15 mL), and acetic acid (250 μL) was added cyclopentanone (314 μL, 3.54 mmol), followed by sodium cyanoborohydride (371 mg, 5.9 mmol). After stirring at 60° C. for 2 h, the reaction was concentrated, partitioned between dichloromethane/1N sodium carbonate, washed with water/brine, dried over sodium sulfate, and concentrated. The product was purified using prep TLC plates (9:1 dichloromethane:methanol) (25%); Mp 233-237° C.; MS m/z 341 (M+H).

Workup

  1. concentrationthe reaction was concentrated
  2. custompartitioned between dichloromethane/1N sodium carbonate
  3. washwashed with water/brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified

Sources & evidence

ORD record
ord-aec7cd802bcd4df2afccfd0387fd6591
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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