Cyclopentylamine → 5-Chloro-N3-cyclopentylpyridazine-3,4-diamine

HRID 1846005Notes

Reaction equation

HRID 1846005 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[NH2:8].[CH:10]1([NH2:15])[CH2:14][CH2:13][CH2:12][CH2:11]1>O>[Cl:9][C:6]1[C:7]([NH2:8])=[C:2]([NH:15][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 64032013,5-Dichloro-1,4-dihydropyridazin-4-imine

Product 1

HCID 867232335-Chloro-N3-cyclopentylpyridazine-3,4-diamineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

3,5-Dichloropyridazin-4-amine (Preparation 4, 1 g, 6.09 mmol) was added to cyclopentylamine (3.0 mL, 30.41 mmol) and water (1 mL) in a stainless steel sealed container. The mixture was heated for 16 hours at 150° C. The reaction mixture was cooled to room temperature then evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with EtOAc to afford the title compound as yellow solid in 90% yield, 1.17 g.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthen evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with EtOAc

Sources & evidence

ORD record
ord-1f4dc9d1574540559185f6c4003763ef
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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