Acetic Acid → HCID 86653606, compound

HRID 1918263Notes

Reaction equation

HRID 1918263 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
22.5 °C

Procedure

Sunitinib base (4 g) was suspended in n-butanol (12 ml) with stirring at 20-25° C. Then 1.05 eq (0.45 ml) of acetic acid were added observing dissolution and after 1-2′ precipitation of an orange solid. Then methyl tert-butyl ether (80 ml) was added at 20-25° C. within 10 min with stirring, the mixture was cooled to −10° C. in 2 hours. After 16 h at −10° C. the solid was filtered, washed with 2×20 ml of MTBE and dried on the filter for 1 h yielding 4 g of Sunitinib Acetate.

Workup

  1. dissolutiondissolution
  2. customafter 1-2′ precipitation of an orange solid
  3. additionThen methyl tert-butyl ether (80 ml) was added at 20-25° C. within 10 min
  4. stirringwith stirring
  5. temperaturethe mixture was cooled to −10° C. in 2 hours
  6. filtrationAfter 16 h at −10° C. the solid was filtered
  7. washwashed with 2×20 ml of MTBE
  8. customdried on the
  9. filtrationfilter for 1 h

Sources & evidence

ORD record
ord-a59bd2b9b5e14abab7c7b42c88f8c37f
Source dataset
uspto-grants-2013_12
Patent number
US08618309B2

Reaction notes

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