HCID 66715997, compound → HCID 56645594, compound

HRID 876878Notes

Reaction equation

HRID 876878 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:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:20][C:21]4[N:22]([C:24](/[CH:27]=[CH:28]/[C:29](=[O:31])[NH2:30])=[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>[NH2:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:20][C:21]4[N:22]([C:24](/[CH:27]=[CH:28]/[C:29]([NH2:30])=[O:31])=[CH:25][N:26]=4)[N:23]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 66715997HCID 66715997, compound

Product 1

HCID 56645594HCID 56645594, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

162 mg Crude (1-{4-[3-((E)-2-carbamoyl-vinyl)-7-phenyl-imidazo[1,2-b]pyridazin-6-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester were stirred in 10.2 mL 4M hydrogen chloride in dioxane for 16 hours at room temperature. After evaporation of the solvent the residue was dissolved in methanol and given on a PoraPak Rxn CX column. The column was washed with 100 mL methanol and the product was eluted with methanol/NH3 yielding 34 mg (13%) of the title compound which was however strongly contaminated.

Workup

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas dissolved in methanol
  3. washThe column was washed with 100 mL methanol
  4. washthe product was eluted with methanol/NH3 yielding 34 mg (13%) of the title compound which

Sources & evidence

ORD record
ord-2f5dc0d1acce4fa598af87789f2d9254
Source dataset
uspto-grants-2015_03
Patent number
US08987273B2

Reaction notes

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