3,6-Dichloropyridazine → HCID 86686135, compound

HRID 869179Notes

Reaction equation

HRID 869179 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[C:9]([NH2:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH3:10].CCN(C(C)C)C(C)C>[Cl-].[Na+].O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:18][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH3:11])[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 673313,6-DichloropyridazineHCID 68509CumylamineHCID 81531Diisopropylethylamine

Product 1

HCID 86686135HCID 86686135, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
225 °C

Procedure

To a 5 mL microwave reaction vial was added 3,6-dichloropyridazine (544 mg, 3.7 mmol, 1.0 equiv), cumylamine (500 mg, 3.7 mmol, 1.0 equiv), and DIPEA (640 μL, 3.7 mmol, 1.0 equiv). The reaction was heated in a microwave reactor to 225° C. for 15 min and then diluted with brine (20 mL) and extracted with ethyl acetate (40 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by silica gel column chromatography (20% EtOAc/hexanes) to yield 48 mg (5%) of 6-chloro-N-(2-phenylpropan-2-yl)pyridazin-3-amine as a white solid.

Workup

  1. customTo a 5 mL microwave reaction
  2. extractionextracted with ethyl acetate (40 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude solid that
  7. customwas purified by silica gel column chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5feadd1b022847329efd48c161eb7418
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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