Hydrochloric Acid → HCID 56645180, compound

HRID 876875Notes

Reaction equation

HRID 876875 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:20][C:21]4[N:22]([C:24]([C:28]5[CH:33]=[CH:32][CH:31]=[C:30]([C:34](=[O:36])[NH2:35])[CH:29]=5)=[C:25]([CH3:27])[N:26]=4)[N:23]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl>O1CCOCC1>[NH2:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[CH:20][C:21]4[N:22]([C:24]([C:28]5[CH:29]=[C:30]([CH:31]=[CH:32][CH:33]=5)[C:34]([NH2:35])=[O:36])=[C:25]([CH3:27])[N:26]=4)[N:23]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86692120HCID 86692120, compound

Product 1

HCID 56645180HCID 56645180, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

210 mg Crude (1-{4-[3-(3-carbamoyl-phenyl)-2-methyl-7-phenyl-imidazo[1,2-b]pyridazin-6-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester, intermediate example Int-4-0, were stirred with 15 mL 4M hydrogen chloride in dioxane over night at room temperature. The solvent was evaporated and the residue was dissolved in methanol/dichloromethane. Methyl-tert.butylether was added until the product precipitated. The reaction mixture was stirred for one hour and the precipitate was sucked off. The crystals were dissolved in methanol and given on a ForaPak Rxn CX column. The column was washed with 100 mL methanol and the product was eluted with methanol/NH3. After evaporation of the solvents the residue was purified by HPLC to yield 39.3 mg of the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in methanol/dichloromethane
  3. additionMethyl-tert.butylether was added until the product
  4. customprecipitated
  5. dissolutionThe crystals were dissolved in methanol
  6. washThe column was washed with 100 mL methanol
  7. washthe product was eluted with methanol/NH3
  8. customAfter evaporation of the solvents the residue
  9. customwas purified by HPLC

Sources & evidence

ORD record
ord-783af22134604e16a3f8529d041561f4
Source dataset
uspto-grants-2015_03
Patent number
US08987273B2

Reaction notes

Loading…