3,6-Dibromopyridazine → Ammonia

HRID 2353197Notes

Reaction equation

HRID 2353197 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][NH:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[N:17]=[N:18][C:19](Br)=[CH:20][CH:21]=1>O1CCOCC1>[NH3:8].[Br:15][C:16]1[N:17]=[N:18][C:19]([N:11]2[CH2:10][C@@H:9]3[CH2:14][C@H:12]2[CH2:13][N:8]3[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 2488523,6-DibromopyridazineHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 2

HCID 222AmmoniaHCID 86598713HCID 86598713, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of tert-butyl-(1S,4S)-2,5-diazabicyclo-[2.2.1]-heptane-2-carboxylate (3.0 g; 15.1 mmol), 3,6-dibromopyridazine (3.6 g; 15.1 mmol) and dioxane (15 ml) was stirred for 3 days at 90° C. The crude product salt was filtered. Aqueous sodium hydroxide (50 ml; 1 M) was added to the solid material. The mixture was extracted with dichloromethane (3×50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 1.71 g (32%).

Workup

  1. filtrationThe crude product salt was filtered
  2. additionAqueous sodium hydroxide (50 ml; 1 M) was added to the solid material
  3. extractionThe mixture was extracted with dichloromethane (3×50 ml)

Sources & evidence

ORD record
ord-df73c1ed0ac44d8f9f5ac9d2137a5bc1
Source dataset
uspto-grants-2010_07
Patent number
US07750011B2

Reaction notes

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