Hydrochloric Acid → HCID 56644349, compound

HRID 876874Notes

Reaction equation

HRID 876874 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:27]5[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=5)=[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>[CH3:36][S:33]([C:30]1[CH:31]=[CH:32][C:27]([C:24]2[N:22]3[N:23]=[C:18]([C:15]4[CH:14]=[CH:13][C:12]([C:8]5([NH2:7])[CH2:11][CH2:10][CH2:9]5)=[CH:17][CH:16]=4)[C:19]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:20][C:21]3=[N:26][CH:25]=2)=[CH:28][CH:29]=1)(=[O:35])=[O:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66714031HCID 66714031, compound

Product 1

HCID 56644349HCID 56644349, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

120 mg (0.2 mmol) (1-{4-[3-(4-Methanesulfonyl-phenyl)-7-phenyl-imidazo[1,2-b]pyridazin-6-yl]-phenyl}-cyclobutyl)-carbamic acid tert.-butyl ester, intermediate example Int-3-2, were stirred with 10 mL 4M hydrogen chloride in dioxane for 23 hours at room temperature. The solvent was evaporated and the residue was treated with saturated sodium bicarbonate solution (pH 9). After stirring for two hours 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, brine, dried, filtrated and the solvent was evaporated. The crude product (97.8 mg) was purified by HPLC to yield 20.8 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, brine
  9. customdried
  10. filtrationfiltrated
  11. customthe solvent was evaporated
  12. customThe crude product (97.8 mg) was purified by HPLC

Sources & evidence

ORD record
ord-c66c126ea18f4624906b7c83d42898c5
Source dataset
uspto-grants-2015_03
Patent number
US08987273B2

Reaction notes

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