Hydrochloric Acid → HCID 44599975, compound

HRID 1915091Notes

Reaction equation

HRID 1915091 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([O:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([Cl:32])=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=3)=[O:20])=[CH:16][CH:17]=2)[CH:8]=[CH:9][N:10]=1)=[O:4].[ClH:33].C(OC(C)C)(C)C>CO>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([Cl:32])=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:27]=3)=[O:20])=[CH:14][CH:13]=2)[CH:8]=[CH:9][N:10]=1)=[O:4].[ClH:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 216239Sorafenib

Product 1

HCID 44599975HCID 44599975, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (35 mL) was added to a reaction vessel containing sorafenib free base (7.0 g) and the reaction mixture was stirred for about 5 minutes. Methanolic HCl (35 mL) was added drop-wise to the above reaction mixture at 0° C. The reaction mixture was stirred for about 1 hour. Diisopropyl ether (70 mL) was added. The reaction mixture was stirred for about 1 hour. The solid was filtered and dried under reduced pressure at about 50° C. for about 3 hours. The solid was triturated with toluene (20 mL) and the reaction mixture was concentrated. The solid was washed with toluene (2×20 mL) and dried under reduced pressure at about 30° C. for about 24 hours to obtain sorafenib hydrochloride.

Workup

  1. stirringThe reaction mixture was stirred for about 1 hour
  2. stirringThe reaction mixture was stirred for about 1 hour
  3. filtrationThe solid was filtered
  4. customdried under reduced pressure at about 50° C. for about 3 hours
  5. customThe solid was triturated with toluene (20 mL)
  6. concentrationthe reaction mixture was concentrated
  7. washThe solid was washed with toluene (2×20 mL)
  8. customdried under reduced pressure at about 30° C. for about 24 hours

Sources & evidence

ORD record
ord-ae0360cabf474be1ab442973e01d9fd2
Source dataset
uspto-grants-2013_12
Patent number
US08614329B2

Reaction notes

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