Hydrazine hydrate (1:1) → HCID 86696530, compound

HRID 1615930Notes

Reaction equation

HRID 1615930 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([N:12]([CH2:14][C@@H:15]2[CH2:17][C@H:16]2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH3:13])[CH:5]=[CH:4][N:3]=1.O.[NH2:26][NH2:27]>O1CCOCC1>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C@@H:16]2[CH2:17][C@H:15]2[CH2:14][N:12]([CH3:13])[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:26][NH2:27])[C:7]=2[C:8]([F:11])([F:10])[F:9])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86696528HCID 86696528, compound

Product 1

HCID 86696530HCID 86696530, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of trans 2-chloro-N-((2-(4-fluorophenyl)cyclopropyl)methyl)-N-methyl-3-(trifluoromethyl)pyridin-4-amine (1.2 g, 3.34 mmol) and hydrazine hydrate (3.32 mL, 66.9 mmol) in dioxane (20 mL) was heated to reflux under nitrogen for 6 h. The reaction mixture was concentrated. The reaction mixture was diluted with EtOAc and washed with aqueous sodium bicarbonate. The aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were washed with aqueous sodium bicarbonate (2×20 mL) and brine (20 mL), dried over magnesium sulfate, and concentrated to give trans-N-((2-(4-fluorophenyl)cyclopropyl)methyl)-2-hydrazinyl-N-methyl-3-(trifluoromethyl)pyridin-4-amine (1.1 g, 80% yield), which was used for the next reaction without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 6 h
  3. concentrationThe reaction mixture was concentrated
  4. additionThe reaction mixture was diluted with EtOAc
  5. washwashed with aqueous sodium bicarbonate
  6. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  7. washThe combined organic layers were washed with aqueous sodium bicarbonate (2×20 mL) and brine (20 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-262ceddfe3c44d1f862e9670c5e3f532
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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