Hydrazine hydrate (1:1) → HCID 67453629, compound

HRID 869155Notes

Reaction equation

HRID 869155 reaction equation
Cl[C:2]1[C:7]([C:8]2[N:13]=[N:12][C:11]([NH:14][CH2:15][C:16]3([C:20]4[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=4)[CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.O.[NH2:28][NH2:29].O1CCOCC1>C(OCC)(=O)C>[F:26][C:25]1[C:20]([C:16]2([CH2:15][NH:14][C:11]3[N:12]=[N:13][C:8]([C:7]4[C:2]([NH:28][NH2:29])=[N:3][CH:4]=[CH:5][CH:6]=4)=[CH:9][CH:10]=3)[CH2:19][CH2:18][CH2:17]2)=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 312751,4-DioxaneHCID 86686130HCID 86686130, compound

Product 1

HCID 67453629HCID 67453629, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

To a 5 mL microwave reaction vessel was added 6-(2-chloropyridin-3-yl)-N-((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)pyridazin-3-amine (750 mg, 2.0 mmol), hydrazine hydrate (1 mL), and dioxane (4 mL). The reaction was heated in a microwave reactor to 160° C. for 15 min, then diluted with ethyl acetate (50 mL), and washed with brine (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by reverse phase column chromatography to give 150 mg of N-((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)-6-(2-hydrazinylpyridin-3-yl)pyridazin-3-amine as an off-white solid. The isolated product was then dissolved in methanol and added to a vial containing ˜1 mL of Raney Nickel suspension in water. The mixture was then stirred under 50 psi of hydrogen for 2 h. The reaction was then filtered, concentrated, and purified by reverse phase column chromatography to give 10 mg (88%) of 6-(2-aminopyridin-3-yl)-N-((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)pyridazin-3-amine as an off-white solid, m/z=351.1 [M+H].

Workup

  1. washwashed with brine (20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude solid that
  6. customwas purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-cc98b156eb94451f9bb33a6c946ce874
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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