HCID 86692122, compound → HCID 56645597, compound

HRID 876884Notes

Reaction equation

HRID 876884 reaction equation
[CH3:1][O:2][C:3](=[O:40])/[CH:4]=[CH:5]/[C:6]1[N:10]2[N:11]=[C:12]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4([NH:31]C(OC(C)(C)C)=O)[CH2:30][CH2:29][CH2:28]4)=[CH:23][CH:22]=3)[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:14][C:9]2=[N:8][C:7]=1[CH3:39]>Cl.O1CCOCC1>[CH3:1][O:2][C:3](=[O:40])/[CH:4]=[CH:5]/[C:6]1[N:10]2[N:11]=[C:12]([C:21]3[CH:22]=[CH:23][C:24]([C:27]4([NH2:31])[CH2:30][CH2:29][CH2:28]4)=[CH:25][CH:26]=3)[C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:14][C:9]2=[N:8][C:7]=1[CH3:39]

Participants

4

Reactant 1

HCID 86692122HCID 86692122, compound

Product 1

HCID 56645597HCID 56645597, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

299 mg Of the crude (E)-3-{6-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-2-methyl-7-phenyl-imidazo[1,2-b]pyridazin-3-yl}-acrylic acid methyl ester were stirred in 17.6 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 (236 mg) was purified by HPLC to yield 40 mg of the title compound.

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 (236 mg) was purified by HPLC

Sources & evidence

ORD record
ord-c4e40c4d53bc495caee3264497eb5e82
Source dataset
uspto-grants-2015_03
Patent number
US08987273B2

Reaction notes

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