Choline → HCID 131734373, compound

HRID 1507461Notes

Reaction equation

HRID 1507461 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:34][CH2:35][CH2:36][N+:37]([CH3:40])([CH3:39])[CH3:38]>CC(C)=O>[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:34][CH2:35][CH2:36][N+:37]([CH3:40])([CH3:39])[CH3:38]

Participants

4

Reactant 2

HCID 305CholineHCID 42611257Vemurafenib

Product 1

HCID 131734373HCID 131734373, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
35 °C

Procedure

To a stirred suspension of Vemurafenib base (1.5 g, 3.1 mmol) and 15 ml acetone (T=30-35° C.), 0.9 ml (3.1 mmol) choline (45% in methanol) was added. The obtained solution was stirred for 5 min at 35° C. then cooled to 5° C., stirred at this temperature for 30 min and then allowed to warm to RT. During overnightstirring in the open vial, the solvent evaporated. To the oily residue, 5 ml ethanol was added. The mixture was placed in an ultrasonic bath until a clear solution was obtained. After the solution was stored in the refrigerator for 3 days, a precipitate was formed which was filtered off, washed with 2 ml ethanol and dried at RT O/N. 0.54 g (yield: 29.7%) Vemurafenib choline salt was isolated in high purity (HPLC/UV: 99.4 area %).

Workup

  1. additionwas added
  2. temperaturethen cooled to 5° C.
  3. stirringstirred at this temperature for 30 min
  4. temperatureto warm to RT
  5. customthe solvent evaporated
  6. additionTo the oily residue, 5 ml ethanol was added
  7. customThe mixture was placed in an ultrasonic bath until a clear solution
  8. customwas obtained
  9. waitAfter the solution was stored in the refrigerator for 3 days
  10. customa precipitate was formed which
  11. filtrationwas filtered off
  12. washwashed with 2 ml ethanol
  13. customdried at RT O/N

Sources & evidence

ORD record
ord-59c2d086cd3745a4a7534d38c4a575cc
Source dataset
uspto-grants-2015_12
Patent number
US09221815B2

Reaction notes

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