Hydrazine hydrate (1:1) → HCID 57978019, compound

HRID 1865826Notes

Reaction equation

HRID 1865826 reaction equation
Cl[C:2]1[C:3]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[C:4]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[C:5](=[O:20])[N:6]([CH2:8][C:9]2[C:10]([CH3:19])=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)[N:7]=1.O.[NH2:35][NH2:36]>>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([C:3]2[C:2]([NH:35][NH2:36])=[N:7][N:6]([CH2:8][C:9]3[C:10]([CH3:19])=[N:11][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:13][CH:14]=3)[C:5](=[O:20])[C:4]=2[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57978000HCID 57978000, compound

Product 1

HCID 57978019HCID 57978019, compound

Conditions

Temperature
130 °C

Procedure

To a round bottom flask was added 6-chloro-5-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-4-(pyridin-4-yl)pyridazin-3(2H)-one (900 mg, 1.833 mmol), 1-BuOH (2 ml) and hydrazine hydrate (5 ml). The reaction was heated to 130° C. and stirred at that temperature for 8 hrs. After this time the reaction was cooled to rt and concentrated under reduced pressure. The reaction was poured into a separatory funnel and partitioned between EtOAc (50 ml) and water (20 ml). The layers were separated and the organic layer was washed with water (20 ml) and saturated aqueous NaCl (20 ml). The organic layer was then slurried with MgSO4 to remove excess water, filtered and concentrated to give the product 5-(4-chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-4-(pyridin-4-yl)pyridazin-3(2H)-one as yellow solid. HPLC retention time (method A) 1.138 min; LCMS (M+H)=487.1.

Workup

  1. temperatureAfter this time the reaction was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. additionThe reaction was poured into a separatory funnel
  4. custompartitioned between EtOAc (50 ml) and water (20 ml)
  5. customThe layers were separated
  6. washthe organic layer was washed with water (20 ml) and saturated aqueous NaCl (20 ml)
  7. customto remove excess water
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b21f5c8b4d37462caca859b6a0527251
Source dataset
uspto-grants-2009_12
Patent number
US07629342B2

Reaction notes

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