Water → (6-(5-Cyclopropylisoxazol-3-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamine

HRID 1513832Notes

Reaction equation

HRID 1513832 reaction equation
C(C1C=CC2[N:7](C(CNC(=O)OC(C)(C)C)=NN=2)N=1)=O.[CH:21]([C:23]1[CH:24]=[CH:25][C:26]2[N:27]([C:29]([CH2:32][NH:33]C(=O)OC(C)(C)C)=[N:30][N:31]=2)[N:28]=1)=[CH2:22].O.I([O-])(=O)(=O)=O.[Na+].[CH2:48]1[CH2:52][O:51][CH2:50][CH2:49]1>[Os](=O)(=O)(=O)=O>[CH:48]1([C:52]2[O:51][N:7]=[C:21]([C:23]3[CH:24]=[CH:25][C:26]4[N:27]([C:29]([CH2:32][NH2:33])=[N:30][N:31]=4)[N:28]=3)[CH:22]=2)[CH2:49][CH2:50]1

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 57691111Tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamateHCID 57691367Tert-butyl (6-vinyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Product 1

HCID 57691172(6-(5-Cyclopropylisoxazol-3-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamineYield 72%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate. Tert-butyl (6-vinyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (485 mg, 1.76 mmol) was dissolved in 5 mL of THF and 5 mL of water then osmium tetroxide (0.687 mL (4% water solution), 0.0176 mmol) was added and stirred for 5 min. Sodium periodate was added (141, 3.53 mmol) and the reaction was stirred for 2 h. The reaction was then extracted with dichloromethane (3×10 mL), dried over Na2SO4 and concentrated. Purification via MPLC (DCM/MeOH+1% NH4OH) afforded title compound as a tan solid (350 mg, 72% yield).

Workup

  1. stirringthe reaction was stirred for 2 h
  2. extractionThe reaction was then extracted with dichloromethane (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification via MPLC (DCM/MeOH+1% NH4OH)

Sources & evidence

ORD record
ord-aeab636a104141cc97676e17743cd511
Source dataset
uspto-grants-2012_07
Patent number
US08217177B2

Reaction notes

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