Hydrochloric Acid → 1-[4-(6-Ethoxy-7,8-dimethyl-3-phenylimidazo[1,2-b]pyridazin-2-yl)phenyl]-cyclobutanamine

HRID 1501365Notes

Reaction equation

HRID 1501365 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([CH3:38])=[C:6]([CH3:37])[C:7]2[N:8]([C:10]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([NH:23]C(=O)OC(C)(C)C)[CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)[N:12]=2)[N:9]=1)[CH3:2].CO.Cl.O1CCOCC1>C(Cl)Cl>[CH2:1]([O:3][C:4]1[C:5]([CH3:38])=[C:6]([CH3:37])[C:7]2[N:8]([C:10]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([C:19]4([NH2:23])[CH2:20][CH2:21][CH2:22]4)=[CH:17][CH:18]=3)[N:12]=2)[N:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 70856688HCID 70856688, compound

Product 1

HCID 708178331-[4-(6-Ethoxy-7,8-dimethyl-3-phenylimidazo[1,2-b]pyridazin-2-yl)phenyl]-cyclobutanamineYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of the tert-butyl {1-[4-(6-ethoxy-7,8-dimethyl-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-36 (210 mg, 0.410 mmol, 1.0 eq) in DCM (2.64 mL) and MeOH (1.66 mL) was added a solution of 4 M hydrogen chloride in dioxane (2.05 mL, 8.19 mmol, 20.0 eq) and the mixture was stirred overnight at rt. The mixture was poured onto ice, made alkaline, treated with DCM and filtered through a phase separator. The volatile components of the organic phase were removed in vacuo to give 145 mg (82% yield) of the title compound.

Workup

  1. customwas prepared in a manner analgous to
  2. additionThe mixture was poured onto ice
  3. filtrationfiltered through a phase separator
  4. customThe volatile components of the organic phase were removed in vacuo

Sources & evidence

ORD record
ord-21df9bc34e2c49ed829ccbf7c8a82588
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

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