HCID 66714355, compound → HCID 56645596, compound

HRID 876882Notes

Reaction equation

HRID 876882 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:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:20][C:21]4[N:22]([C:24](/[CH:28]=[CH:29]/[C:30](=[O:32])[NH2:31])=[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:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[CH:20][C:21]4[N:22]([C:24](/[CH:28]=[CH:29]/[C:30]([NH2:31])=[O:32])=[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 1

HCID 66714355HCID 66714355, compound

Product 1

HCID 56645596HCID 56645596, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

247 mg Of the crude (1-{4-[3-((E)-2-carbamoyl-vinyl)-2-methyl-7-phenyl-imidazo[1,2-b]pyridazin-6-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester were stirred in 15 mL 4M hydrogen chloride in dioxane for 22 hours at room temperature. The solvent was evaporated and the residue was treated with saturated sodium bicarbonate solution (pH 9). After stirring for one hour 100 mL dichloromethane were added and stirring was continued for one hour. The organic phase was separated and the aqueous phase was extracted once more with dichloromethane (50 mL). The combined organic extracts were washed with water and brine, dried, filtrated and the solvent was evaporated. The crude product (197.2 mg) was purified by HPLC to yield 50.3 mg of the title compound which was however contaminated.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was treated with saturated sodium bicarbonate solution (pH 9)
  3. additionwere added
  4. stirringstirring
  5. waitwas continued for one hour
  6. customThe organic phase was separated
  7. extractionthe aqueous phase was extracted once more with dichloromethane (50 mL)
  8. washThe combined organic extracts were washed with water and brine
  9. customdried
  10. filtrationfiltrated
  11. customthe solvent was evaporated
  12. customThe crude product (197.2 mg) was purified by HPLC

Sources & evidence

ORD record
ord-cfcd9914a9dd4529ac48c321d69abfbb
Source dataset
uspto-grants-2015_03
Patent number
US08987273B2

Reaction notes

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