6-Amino-3-chloropyridazine → 6-((1S,4S)-5-Methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-pyridazin-3-ylamine

HRID 1431152Notes

Reaction equation

HRID 1431152 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[CH3:9][N:10]1[CH2:15][C@@H:14]2[CH2:16][C@H:11]1[CH2:12][NH:13]2>C(Cl)Cl>[CH3:9][N:10]1[CH2:15][C@@H:14]2[CH2:16][C@H:11]1[CH2:12][N:13]2[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 11029795(1S,4S)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 667430796-((1S,4S)-5-Methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-pyridazin-3-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

6-Chloropyridazin-3-amine (200 mg, 1.54 mmol, Eq: 1.00) and (1S,4S)-2-methyl-2,5-diazabicyclo[2.2.1]heptane (693 mg, 6.18 mmol, Eq: 4.00) were combined in a small round bottom flask and heated at 200° C. for 2 hours. The dark glassy residue was dissolved in DCM and purified by chromatography using a gradient of 0% to 25% methanol (with 2.5% ammonium hydroxide) in DCM to give about 100 mg (31.6%) of a brown, viscous oil.

Workup

  1. custompurified by chromatography
  2. customto give about 100 mg (31.6%) of a brown, viscous oil

Sources & evidence

ORD record
ord-02d80ceeed7b4968b338a47a688e8aed
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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