Water → HCID 68432076, compound

HRID 2092090Notes

Reaction equation

HRID 2092090 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=O)[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:29])[CH3:28])[C@H:22]1[CH3:30].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S([O-])([O-])(=O)=O.[Mg+2].O1CC[CH2:46][CH2:45]1>C(OCC)(=O)C>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][CH2:10][NH:12][CH:13]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:45][CH3:46])[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:29])[CH3:28])[C@H:22]1[CH3:30]

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 68431201HCID 68431201, compound

Product 1

HCID 68432076HCID 68432076, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(5-Chloro-6-oxo-4-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-1(6H)-yl)-N-(pyridin-4-ylmethyl)acetamide (40 mg, 0.0873 mmol) was added to lithium aluminum hydride (4.3 mg, 0.104 mmol) in tetrahydrofuran (1 mL) at 0° C., and the resulting reaction solution was stirred at room temperature for 1.5 hours. After completion of the reaction, the reaction solution was mixed with water, ethyl acetate and anhydrous magnesium sulfate and filtered, and the filtrate was evaporated under reduced pressure. The resulting residue was purified by preparative thin layer chromatography (chloroform/methanol=13/1) to give the desired product (9.5 mg, 25% yield).

Workup

  1. customthe resulting reaction solution
  2. customAfter completion of the reaction
  3. filtrationfiltered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe resulting residue was purified by preparative thin layer chromatography (chloroform/methanol=13/1)

Sources & evidence

ORD record
ord-de60c616c71646d5b4fb226fd965c25a
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

Loading…