Tert-Butylamine → N-tert-butyl-6-chloropyridazine-3-carboxamide

HRID 586798Notes

Reaction equation

HRID 586798 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:11]([NH:15][C:8]([C:5]1[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:10])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 516892Sodium BicarbonateHCID 64157626-chloropyridazine-3-carboxylic Acid

Product 1

HCID 12059835N-tert-butyl-6-chloropyridazine-3-carboxamideYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-chloro-3-pyridazinecarboxylic acid (0.12 g, 0.76 mmol) in methylene chloride (15 ml) were added t-butylamine (0.21 ml, 2.0 mmol) and N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.24 g, 0.93 mmol), and stirred overnight. The reaction mixture was added to saturated aqueous NaHCO3 and extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel chromatography (hexane/ethyl acetate=2/1) to give the title compound (0.080 g; 49%).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-692f00977b6245a681161be3d1ac57e8
Source dataset
uspto-grants-2005_08
Patent number
US06936736B2

Reaction notes

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