Ethyl Acetate → HCID 68431929, compound

HRID 2092102Notes

Reaction equation

HRID 2092102 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:27][C@@H:28]1[CH2:33][C@@H:32]2[CH2:34][C@@H:30]([C:31]2([CH3:36])[CH3:35])[C@H:29]1[CH3:37].C(OCC)(=O)C>Cl.O1CCOCC1>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:27][C@@H:28]1[CH2:33][C@@H:32]2[CH2:34][C@@H:30]([C:31]2([CH3:36])[CH3:35])[C@H:29]1[CH3:37]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 68431327HCID 68431327, compound

Product 1

HCID 68431929HCID 68431929, compound

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

t-Butyl 4-[({[5-bromo-6-oxo-4-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-1(6H)-yl]acetyl}amino)methyl]piperidine-1-carboxylate (34.4 mg, 0.06 mmol) was dissolved in 4 M hydrogen chloride/1,4-dioxane (1 mL) and stirred at room temperature for 2 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=50/1) to give the desired product.

Workup

  1. additionwas added
  2. washthe organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-5a41ceeb925b4b58a924e42495b590d1
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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