Acetic Acid → 5-Chloro-N3-isopropylpyridazine-3,4-diamine

HRID 1845999Notes

Reaction equation

HRID 1845999 reaction equation
CC(O)=O.Cl[C:6]1[N:7]=[N:8][CH:9]=[C:10]([Cl:13])[C:11]=1[NH2:12].[CH:14]([NH2:17])([CH3:16])[CH3:15]>CO>[Cl:13][C:10]1[C:11]([NH2:12])=[C:6]([NH:17][CH:14]([CH3:16])[CH3:15])[N:7]=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6363IsopropylamineHCID 64032013,5-Dichloro-1,4-dihydropyridazin-4-imine

Product 1

HCID 867232295-Chloro-N3-isopropylpyridazine-3,4-diamineYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

HOAc (2.47 mL, 42.7 mmol) was added dropwise to a mixture of 3,5-dichloropyridazin-4-amine (Preparation 4, 1000 mg, 6.098 mmol) and isopropylamine (7.27 mL, 85.4 mmol) cooled to 0° C. The resulting solid/suspension was heated under microwave irradiation at 105° C. for 5 hours. The reaction mixture was dissolved in minimum amount of MeOH and purified by silica gel column chromatography eluting with EtOAc:heptane: 10%-90% to provide the title compound as a slightly brownish solid in 74% yield, 2.52 g.

Workup

  1. temperatureThe resulting solid/suspension was heated under microwave irradiation at 105° C. for 5 hours
  2. custompurified by silica gel column chromatography
  3. washeluting with EtOAc

Sources & evidence

ORD record
ord-de2b32e472a24435bb92dfa8ddeecd31
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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