Sodium Hydroxide → HCID 68429191, compound

HRID 2092110Notes

Reaction equation

HRID 2092110 reaction equation
[Cl:1][C:2]1[C:3](=[O:33])[N:4]([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:24][CH:23]=2)=[O:21])[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:17])[CH3:16])[C@H:10]1[CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:3](=[O:33])[N:4]([CH2:19][CH:20]([C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:24][CH:23]=2)[OH:21])[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:16])[CH3:17])[C@H:10]1[CH3:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68429248HCID 68429248, compound

Product 1

HCID 68429191HCID 68429191, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Chloro-2-{2-[4-(diethylamino)phenyl]-2-oxoethyl-}-5-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-3(2H)-one (42 mg, 0.0891 mmol) in tetrahydrofuran (2 mL) was added dropwise to lithium aluminum hydride (11 mg, 0.315 mmol) in tetrahydrofuran (2 mL) at 0° C. and stirred at room temperature for 10 minutes. After completion of the reaction, the reaction solution was mixed with aqueous sodium hydroxide, anhydrous, sodium sulfate, then filtered and evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography (hexane/ethyl acetate=1/1) to give the desired product (14 mg, 33% yield).

Workup

  1. customAfter completion of the reaction
  2. filtrationanhydrous, sodium sulfate, then filtered
  3. customevaporated under reduced pressure
  4. customThe residue was purified by preparative thin layer chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-9673960c40c04f71b80273a626052013
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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