Hydrochloric Acid → HCID 70817875, compound

HRID 1501351Notes

Reaction equation

HRID 1501351 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4([NH:22]C(=O)OC(C)(C)C)[CH2:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)[N:11]=2)[N:8]=1)[CH3:2].Cl.O1CCOCC1.[OH-].[Na+]>C(Cl)Cl.CO>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4([NH2:22])[CH2:19][CH2:20][CH2:21]4)=[CH:14][CH:13]=3)[N:11]=2)[N:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86716519HCID 86716519, compound

Product 1

HCID 70817875HCID 70817875, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl {1-[4-(6-ethyl-3-phenylimidazo[1,2-b]pyridazin-2-yl)phenyl]cyclobutyl}carbamate that was prepared in a manner analgous to that described for Intermediate Example Int-2 (300 mg, 0.608 mmol, 1.0 eq) in DCM (3.9 mL) and MeOH (2.5 mL) was added a solution of 4 M hydrogen chloride in dioxane (3.0 mL, 12.2 mmol, 20.0 eq) and the mixture was stirred for overnight at rt. The mixture was poured onto ice, made alkaline with aqueous sodium hydroxide (2 N) and extracted with DCM. The combined organic phases were washed with brine, dried and concentrated in vacuo. Purification was achieved by crystallization from diisopropyl ether. The resulting solid was filtered and dried under high vacuum overnight to give 119 mg (52% yield) of the title compound.

Workup

  1. customwas prepared in a manner analgous to
  2. additionThe mixture was poured onto ice
  3. extractionextracted with DCM
  4. washThe combined organic phases were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customPurification
  8. customwas achieved by crystallization from diisopropyl ether
  9. filtrationThe resulting solid was filtered
  10. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-255a1780e0fa4bb89b3a89bc2adbe357
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

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