Ethanol → HCID 131734373, compound

HRID 1507460Notes

Reaction equation

HRID 1507460 reaction equation
[CH3:1][CH2:2][CH2:3][S:4]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([F:33])=[C:12]([C:15]([C:17]2[C:21]3[CH:22]=[C:23]([C:26]4[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=4)[CH:24]=[N:25][C:20]=3[NH:19][CH:18]=2)=[O:16])[C:13]=1[F:14])(=[O:6])=[O:5].[OH-].[OH:35][CH2:36][CH2:37][N+:38]([CH3:41])([CH3:40])[CH3:39].CO.C(O)C>CC(C)=O.CCCCCC>[CH3:1][CH2:2][CH2:3][S:4]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([F:33])=[C:12]([C:15]([C:17]2[C:21]3[CH:22]=[C:23]([C:26]4[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=4)[CH:24]=[N:25][C:20]=3[NH:19][CH:18]=2)=[O:16])[C:13]=1[F:14])(=[O:6])=[O:5].[OH:35][CH2:36][CH2:37][N+:38]([CH3:41])([CH3:40])[CH3:39]

Participants

7

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 31255Choline, hydroxideHCID 42611257Vemurafenib

Product 1

HCID 131734373HCID 131734373, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 8058HexaneCatalystHCID 180AcetoneSolvent

Conditions

Temperature
35 °C

Procedure

Vemurafenib (500 mg, 1.0 mmol) was suspended in 5 mL acetone at 35°. A solution of choline hydroxide in methanol (45%, 270 mg, 1.0 mmol) was added and the resulting mixture was stirred at 35° C. for 5 minutes. Then, the resulting clear solution was cooled to 5° C. over 30 minutes and was stirred in the opened vial overnight at room temperature. An oily residue was obtained and 2 mL ethanol was added. The mixture was sonicated (treated with ultra-sonic energy) until a clear solution was obtained. Two drops of n-hexane were added and the mixture was cooled in a refrigerator for 9 days. The obtained precipitate was filtered, washed with ethanol and dried under normal pressure at room temperature to yield 200 mg (33%) Vemurafenib choline as a white solid. (Purity: 98.4% by HPLC)

Workup

  1. temperatureThen, the resulting clear solution was cooled to 5° C. over 30 minutes
  2. stirringwas stirred in the opened vial overnight at room temperature
  3. customAn oily residue was obtained
  4. customThe mixture was sonicated
  5. addition(treated with ultra-sonic energy) until a clear solution
  6. customwas obtained
  7. temperaturethe mixture was cooled in a refrigerator for 9 days
  8. filtrationThe obtained precipitate was filtered
  9. washwashed with ethanol
  10. customdried under normal pressure at room temperature

Sources & evidence

ORD record
ord-0f781886e70048288d0ffb0e683fbe7c
Source dataset
uspto-grants-2015_12
Patent number
US09221815B2

Reaction notes

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