Hydrochloric Acid → HCID 56644347, compound

HRID 876873Notes

Reaction equation

HRID 876873 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:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:20][C:21]4[N:22]([C:24]([CH3:27])=[CH:25][N:26]=4)[N:23]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl>O1CCOCC1>[CH3:27][C:24]1[N:22]2[N:23]=[C:18]([C:15]3[CH:14]=[CH:13][C:12]([C:8]4([NH2:7])[CH2:11][CH2:10][CH2:9]4)=[CH:17][CH:16]=3)[C:19]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:20][C:21]2=[N:26][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86692117HCID 86692117, compound

Product 1

HCID 56644347HCID 56644347, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

18 mg (0.04 mmol) {1-[4-(3-Methyl-7-phenyl-imidazo[1,2-b]pyridazin-6-yl)-phenyl]-cyclobutyl}-carbamic acid tert.-butyl ester (intermediate example Int-3-0) were dissolved in 01 mL dioxane. 0.4 mL 4M hydrogen chloride in dioxane were added and the mixture was stirred over night at room temperature. The solvent was evaporated and the residue was treated with saturated sodium bicarbonate solution. After stirring for one hour the reaction mixture was extracted three times with ethyl acetate. The combined organic extracts were washed with water and dried (sodium sulfate). After removal of the solvent the residue was purified by chromatography on silicagel (eluents dichloromethane/methanol) and additional HPLC yielding 2.3 mg (14%) of the title compound.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was treated with saturated sodium bicarbonate solution
  3. stirringAfter stirring for one hour the reaction mixture
  4. extractionwas extracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried (sodium sulfate)
  7. customAfter removal of the solvent the residue
  8. customwas purified by chromatography on silicagel (eluents dichloromethane/methanol) and additional HPLC

Sources & evidence

ORD record
ord-37e1a1ce90fe4a49a6dfcc449bd7ff28
Source dataset
uspto-grants-2015_03
Patent number
US08987273B2

Reaction notes

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