Acetone → HCID 131734373, compound

HRID 1507462Notes

Reaction equation

HRID 1507462 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].CC(C)=O.[OH:38][CH2:39][CH2:40][N+:41]([CH3:44])([CH3:43])[CH3:42].C(O)(C)C>C(OC)(C)(C)C.C(OCC)(=O)C>[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:38][CH2:39][CH2:40][N+:41]([CH3:44])([CH3:43])[CH3:42]

Participants

7

Reactant 4

HCID 180AcetoneHCID 305CholineHCID 3776IsopropanolHCID 42611257Vemurafenib

Product 1

HCID 131734373HCID 131734373, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
35 °C

Procedure

To a stirred suspension of 1.5 g Vemurafenib base and 15 ml acetone (T=30-35° C.), 0.9 ml choline (45% in methanol) was added. The obtained solution was stirred for 5 min at 35° C., then cooled to RT and divided into three identical portions. All three portions were stirred O/N in open vials at RT. To the oily residues, 1.5 ml of solvent was added (vial 1: isopropanol, vial 2: ethyl acetate and vial 3: tert. butylmethylether). After treatment in an ultrasonic bath until a clear solution was obtained, the vials were stored in the refrigerator for 6 days, the precipitates were filtered off, washed with 1.5 ml of the same solvent which was used for precipitation and dried O/N at RT.

Workup

  1. additionwas added
  2. temperaturecooled to RT
  3. stirringAll three portions were stirred O/N in open vials at RT
  4. customAfter treatment in an ultrasonic bath until a clear solution was obtained
  5. waitthe vials were stored in the refrigerator for 6 days
  6. filtrationthe precipitates were filtered off
  7. washwashed with 1.5 ml of the same solvent which
  8. customwas used for precipitation
  9. customdried O/N at RT

Sources & evidence

ORD record
ord-08481ff7c99e4737b659f14264547b34
Source dataset
uspto-grants-2015_12
Patent number
US09221815B2

Reaction notes

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