Ethyl Acetate → HCID 68430988, compound

HRID 2092095Notes

Reaction equation

HRID 2092095 reaction equation
[Br: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]=[C:16]([C:20]#[N:21])[CH:15]=2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:22][C@@H:23]1[CH2:28][C@@H:27]2[CH2:29][C@@H:25]([C:26]2([CH3:31])[CH3:30])[C@H:24]1[CH3:32].C(OCC)(=[O:35])C>C(O)C>[Br: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]=[C:16]([C:20]([NH2:21])=[O:35])[CH:15]=2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:22][C@@H:23]1[CH2:28][C@@H:27]2[CH2:29][C@@H:25]([C:26]2([CH3:31])[CH3:30])[C@H:24]1[CH3:32]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 68432060HCID 68432060, compound

Product 1

HCID 68430988HCID 68430988, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2-[5-Bromo-6-oxo-4-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-1(6H)-yl]-N-[(2-cyanopyridin-4-yl)methyl]acetamide (34.0 mg, 0.07 mmol) was dissolved in ethanol/30% aqueous potassium hydroxide (4 mL, 1:1) and stirred at 80° C. for 2 hours. After cooling, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol=8/1) to give the desired product.

Workup

  1. temperatureAfter cooling
  2. washthe organic layer was washed with saturated aqueous ammonium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol=8/1)

Sources & evidence

ORD record
ord-97689874d7ba4fbe91ad2a0a4ea75f11
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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