Hydrazine hydrate (1:1) → 2-(3-Aminopyridin-4-yl)-5-(trifluoromethyl)benzoxazole

HRID 884865Notes

Reaction equation

HRID 884865 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:17]3C(=O)C4=CC=CC=C4C3=O)=[N:8][C:7]=2[CH:28]=1.O.NN>C(O)C>[NH2:17][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:11]=1[C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:30])([F:29])[F:1])=[CH:28][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66880022N-{4-[5-(trifluoromethyl)benzoxazole-2-yl]pyridin-3-yl}phthalimide

Product 1

HCID 668801682-(3-Aminopyridin-4-yl)-5-(trifluoromethyl)benzoxazoleYield 67.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of 0.41 g of N-{4-[5-(trifluoromethyl)benzoxazole-2-yl]pyridin-3-yl}phthalimide and 5 ml of ethanol, 0.3 ml of hydrazine monohydrate was added and stirred at room temperature for 1.5 hours. To the reaction mixture, ethanol was added and filtrated, and the filtrate was concentrated. The residue was diluted with ethyl acetate, and washed with water and then with a saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.19 g of 2-(3-aminopyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 52”).

Workup

  1. additionwas added
  2. filtrationfiltrated
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-86817c99c0884eff9ebc1355e129ea19
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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