Acetic Acid → HCID 86653606, compound

HRID 1918261Notes

Reaction equation

HRID 1918261 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:15]([CH3:16])=[C:14](/[CH:17]=[C:18]2/[C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[NH:26][C:27]/2=[O:28])[NH:13][C:12]=1[CH3:29])=[O:10])[CH2:4][CH3:5].[C:30]([OH:33])(=[O:32])[CH3:31]>C(O)CCC>[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:15]([CH3:16])=[C:14](/[CH:17]=[C:18]2/[C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[NH:26][C:27]/2=[O:28])[NH:13][C:12]=1[CH3:29])=[O:10])[CH2:4][CH3:5].[C:30]([O-:33])(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 5329102Sunitinib

Product 1

HCID 86653606HCID 86653606, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
20 °C

Procedure

Sunitinib base (3 g) was suspended in n-butanol (15 ml) with stirring at 20° C., then 1.05 eq (0.45 ml) of acetic acid were added observing dissolution and after 1-2′ precipitation of an orange solid. The mixture was heated to 60° C. and other 6 ml of n-butanol were added. Then methyl tert-butyl ether (60 ml) was added at 60° C. within 10 min with stirring, the mixture was cooled to −10° C. in 2 hours. After 1 h at −10° C. the solid was filtered, washed with 2×20 ml of MTBE and dried on the filter for 1 h.

Workup

  1. dissolutiondissolution
  2. customafter 1-2′ precipitation of an orange solid
  3. temperatureThe mixture was heated to 60° C.
  4. additionother 6 ml of n-butanol were added
  5. additionThen methyl tert-butyl ether (60 ml) was added at 60° C. within 10 min
  6. stirringwith stirring
  7. temperaturethe mixture was cooled to −10° C. in 2 hours
  8. filtrationAfter 1 h at −10° C. the solid was filtered
  9. washwashed with 2×20 ml of MTBE
  10. customdried on the
  11. filtrationfilter for 1 h.

Sources & evidence

ORD record
ord-44a15548456e4c958d1f74831c61ff8d
Source dataset
uspto-grants-2013_12
Patent number
US08618309B2

Reaction notes

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