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Imatinib derivatives as inhibitors of K562 cells in chronic myeloid leukemia

By Azevedo, Liviane D.; Bastos, Monica M.; Vasconcelos, Flavia C.; Hoelz, Lucas V. B.; Junior, Floriano P. S.; Dantas,
Rafael F.; de Almeida, Ana C. M.; de Oliveira, Andressa Paula; Gomes, Larissa C.; Maia, Raquel C.; Boechat, Nubia
From Medicinal Chemistry Research, 26(11), 2929-2941; 2017
Published by Springer

82%

Products Acetylisatin, 82%, CAS RN: 574-17-4

Reactants Acetic anhydride, CAS RN: 108-24-7
Isatin, CAS RN: 91-56-5
Procedure
1. Add 5-substituted isatin (1 mol) and 20 moles of previously distilled acetic anhydride to
a 100-mL flask equipped with a reflux condenser.

2. Keep the reaction mixture under magnetic stirring at reflux for 2-4 hours until the
reaction id complete.

3. Monitor the reaction by TLC.

4. Cool the reaction mixture in the freezer for 2 hours.

5. Filter the precipitate under vacuum.

6. Wash the precipitate with hexane.

7. Dry the precipitate at room temperature.

8. Recrystallize the solids with hexane and ethyl acetate (1:1) to obtain the 1-
acetylindoline-2,3-dione.

Transformation Acylation of Amides by Acid Derivatives

Acylation of Nitrogen Nucleophiles by Anhydrides or Dicarbonates
Mass Spec GC-MS (70 eV, %): 189 (14); 147 (23); 146 (100); 119 (6); 90 (23).
MP 139-140 °C
CAS Method Number 3-366-CAS-18005221

CASREACT ®: Copyright © 2021 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.