Hydrochloric Acid → 1-{4-[7,8-Dimethyl-6-(methylsulfanyl)-3-phenylimidazo[1,2-b]pyridazin-2-yl]-phenyl}cyclobutanamine

HRID 1501364Notes

Reaction equation

HRID 1501364 reaction equation
[CH3:1][C:2]1[C:7]([S:8][CH3:9])=[N:6][N:5]2[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]=[C:4]2[C:3]=1[CH3:37].CO.Cl.O1CCOCC1>C(Cl)Cl>[CH3:1][C:2]1[C:7]([S:8][CH3:9])=[N:6][N:5]2[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])[CH2:22][CH2:21][CH2:20]4)=[CH:17][CH:18]=3)[N:12]=[C:4]2[C:3]=1[CH3:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 70856623HCID 70856623, compound

Product 1

HCID 708179531-{4-[7,8-Dimethyl-6-(methylsulfanyl)-3-phenylimidazo[1,2-b]pyridazin-2-yl]-phenyl}cyclobutanamineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of the tert-butyl (1-{4-[7,8-dimethyl-6-(methylsulfanyl)-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-35 (95 mg, 0.190 mmol, 1.0 eq) in DCM (1.19 mL) and MeOH (0.75 mL) was added a solution of 4 M hydrogen chloride in dioxane (0.92 mL, 3.69 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 75 mg (94% 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-5aa3c7cfbc1644f7bd64904d81a2dd5d
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

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