Diisopropyl Ether → Sunitinib

HRID 1918265Notes

Reaction equation

HRID 1918265 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([CH3:29])=[C:13](/[CH:17]=[C:18]2/[C:19]3[CH:20]=[C:21]([F:28])[CH:22]=[CH:23][C:24]=3[NH:25][C:26]/2=[O:27])[NH:14][C:15]=1[CH3:16])=[O:10])[CH2:4][CH3:5].C([O-])(=O)C.C(OC(C)C)(C)C>C(O)C>[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([CH3:29])=[C:13](/[CH:17]=[C:18]2/[C:19]3[CH:20]=[C:21]([F:28])[CH:22]=[CH:23][C:24]=3[NH:25][C:26]/2=[O:27])[NH:14][C:15]=1[CH3:16])=[O:10])[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 7914Diisopropyl EtherHCID 86653606HCID 86653606, compound

Product 1

HCID 5329102SunitinibYield 91.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

Sunitinib acetate (1 g) was suspended in absolute ethanol (20 ml) under stirring at 20° C. and the mixture was heated to 40° C. Then diisopropyl ether (40 ml) was added within 10 min with stirring, the mixture was cooled to −10° C. in 2 hours and after 2 h at −10° C. the solid was filtered and dried for 16 hours under vacuum at 75° C. obtaining 0.8 g of orange solid.

Workup

  1. temperaturethe mixture was heated to 40° C
  2. stirringwith stirring
  3. temperaturethe mixture was cooled to −10° C. in 2 hours and after 2 h at −10° C. the solid
  4. filtrationwas filtered
  5. customdried for 16 hours under vacuum at 75° C.

Sources & evidence

ORD record
ord-4fd6283b144748b6b44b43b84095008e
Source dataset
uspto-grants-2013_12
Patent number
US08618309B2

Reaction notes

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