Hydrochloric Acid → HCID 71617851, compound

HRID 60067Notes

Reaction equation

HRID 60067 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].[ClH:34].C(O)C>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].[ClH:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 42611257Vemurafenib

Product 1

HCID 71617851HCID 71617851, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
35 °C

Procedure

Vemurafenib (97.8 g, 199.6 mmol) was suspended in 900 mL acetone and the mixture was warmed to 35° C. While maintaining this temperature, 200 ml of 1.25 M HCl in ethanol (250 mmol HCl, 1.25 equivalents) were added dropwise. A clear solution was obtained. Thereafter, the solution was stirred for another 5 min at 35° C. and then allowed to cool to RT and stirred overnight. The obtained precipitate was filtered, washed with acetone and dried at 40° C. under reduced pressure (30 mbar) for approximately 16 h. Yield: 95.8 g (91%)

Workup

  1. additionwere added dropwise
  2. customA clear solution was obtained
  3. temperatureto cool to RT
  4. stirringstirred overnight
  5. filtrationThe obtained precipitate was filtered
  6. washwashed with acetone
  7. customdried at 40° C. under reduced pressure (30 mbar) for approximately 16 h

Sources & evidence

ORD record
ord-75fcdb390e864aeb93275f77be4177f6
Source dataset
uspto-grants-2016_09
Patent number
US09440971B2

Reaction notes

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