Hydrazine hydrate (1:1) → HCID 86696525, compound

HRID 1615925Notes

Reaction equation

HRID 1615925 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([NH:12][CH2:13][C@H:14]2[CH2:16][C@@H:15]2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:5]=[CH:4][N:3]=1.O.[NH2:25][NH2:26]>O1CCOCC1.CCOC(C)=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C@H:15]2[CH2:16][C@@H:14]2[CH2:13][NH:12][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:25][NH2:26])[C:7]=2[C:8]([F:11])([F:10])[F:9])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86696524HCID 86696524, compound

Product 1

HCID 86696525HCID 86696525, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-N-(((1S,2S)-2-(4-fluorophenyl)cyclopropyl)methyl)-3-(trifluoromethyl)pyridin-4-amine (0.7 g, 2.031 mmol) and hydrazine monohydrate (2.033 g, 40.6 mmol) in dioxane (8 mL) was heated to reflux under nitrogen for 16 h. The reaction mixture was diluted with EtOAc and extracted with aqueous sodium bicarbonate. The aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were washed with aqueous sodium bicarbonate (10 mL) and brine (10 mL), dried over magnesium sulfate, filtered and concentrated under vacuum to give N-(((1S,2S)-2-(4-fluorophenyl)cyclopropyl)methyl)-2-hydrazinyl-3-(trifluoromethyl)pyridin-4-amine (0.7 g, 65%) which was used for the next step without purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 16 h
  3. extractionextracted with aqueous sodium bicarbonate
  4. extractionThe aqueous layer was extracted with EtOAc (2×5 mL)
  5. washThe combined organic layers were washed with aqueous sodium bicarbonate (10 mL) and brine (10 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0475a41caa0f41c08b54c136a9028114
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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