Acetic Anhydride → HCID 66879643, compound

HRID 1913657Notes

Reaction equation

HRID 1913657 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>O>[F:18][C:17]([F:20])([F:19])[C:14]1[CH:15]=[CH:16][C:10]2[O:9][C:8]([C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[NH:1][C:21](=[O:23])[CH3:22])=[N:12][C:11]=2[CH:13]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 668801682-(3-Aminopyridin-4-yl)-5-(trifluoromethyl)benzoxazole

Product 1

HCID 66879643HCID 66879643, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.28 g of 2-(3-aminopyridin-4-yl)-5-(trifluoromethyl)benzoxazole and 3 ml of acetic anhydride was stirred while heating at 60° C. for two hours. The reaction mixture was cooled to room temperature, and then water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with ethyl acetate to give 0.17 g of N-[4-(5-trifluoromethylbenzoxazole-2-yl)pyridin-3-yl]acetamide (hereinafter, referred to as “active compound 82”).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-e823de3f942240b7a3b1becc25d35735
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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