Morpholine → HCID 18314524, compound

HRID 277335Notes

Reaction equation

HRID 277335 reaction equation
Cl[C:2]1[C:3]([CH:17]2[CH2:20][CH2:19][CH2:18]2)=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:10]=2)[N:7]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(N(CC)CC)C>O1CCOCC1>[CH:17]1([C:3]2[C:2]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:7][N:6]3[C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:9][N:10]=[C:5]3[CH:4]=2)[CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 110005936-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 18314524HCID 18314524, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine (100 mg, 0.35 mmol), morpholine (154 mg, 1.8 mmol) and triethylamine (178 mg, 1.8 mmol) were heated in 1,4 dioxane (6 ml) in a sealed tube at 90° C. for 24 h. The reaction mixture was partitioned (ethyl acetate/water). The organic layer was washed (water, brine), dried (MgSO4) and was evaporated in vacuo. The residue was purified by chromatography on silica gel, eluting with ethyl acetate to give the title compound. 1H NMR (250 MHz, CDCl3) δ 1.96-2.88 (1H, m), 2.48 (2H, m), 3.25-3.28 (4H, m), 3.70-3.76 (1H, m), 3.90-3.94 (4H, m), 7.52-7.55 (3H, m), 7.98 (1H, s), 8.49 (2H, s); MS (ES+) m/e 336 [MH]+.

Workup

  1. customThe reaction mixture was partitioned (ethyl acetate/water)
  2. washThe organic layer was washed (water, brine)
  3. dry with materialdried (MgSO4)
  4. customwas evaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-266375be3ade44fd8149273d8cf427b5
Source dataset
uspto-grants-2002_03
Patent number
US06355798B1

Reaction notes

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