Ammonium formate → tert-Butyl 3-(8-morpholinoimidazo[1,2-b]pyridazin-2-yl)azetidine-1-carboxylate

HRID 718590Notes

Reaction equation

HRID 718590 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[N:6]([CH:8]=[C:9]([CH:11]3[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]3)[N:10]=2)[N:7]=1.C([O-])=O.[NH4+]>C1COCC1.CO.CCOC(C)=O.[Pd]>[O:25]1[CH2:24][CH2:23][N:22]([C:4]2[C:5]3[N:6]([CH:8]=[C:9]([CH:11]4[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]4)[N:10]=3)[N:7]=[CH:2][CH:3]=2)[CH2:27][CH2:26]1

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 117732465tert-Butyl 3-(6-chloro-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)azetidine-1-carboxylate

Product 1

HCID 117732466tert-Butyl 3-(8-morpholinoimidazo[1,2-b]pyridazin-2-yl)azetidine-1-carboxylate

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Compound 19b (430 mg, 1.09 mmol) and ammonium formate (344 mg, 5.45 mmol) were placed in a 20 mL vial equipped with a stir bar and dissolved in a mixture of THF (8 mL) and MeOH (4 mL). 10% Pd/C (116 mg, 0.109 mmol) was then added. The reaction mixture was stirred at 70° C. for 3 h, cooled to rt, and filtered through a pad of diatomaceous earth. The solids were washed with MeOH (2×10 mL). The combined filtrates were concentrated under reduced pressure and the residue obtained was dissolved in EtOAc (100 mL) and washed with water (2×25 mL) and brine (25 mL). The combined aqueous washings were extracted once with EtOAc (25 mL) and the organic extracts were combined, dried over MgSO4, and filtered. The solvent was removed under reduced pressure to obtain compound 19c. Mass Spectrum (LCMS, ESI pos.): Calcd. for C19H25N5O3: 360.2 (M+H). found: 360.3.

Workup

  1. customvial equipped with a stir bar
  2. temperaturecooled to rt
  3. filtrationfiltered through a pad of diatomaceous earth
  4. washThe solids were washed with MeOH (2×10 mL)
  5. concentrationThe combined filtrates were concentrated under reduced pressure
  6. customthe residue obtained
  7. washwashed with water (2×25 mL) and brine (25 mL)
  8. extractionThe combined aqueous washings were extracted once with EtOAc (25 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f960491191e4446cab8d80f9b24aca4c
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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