Hydrogen Bromide → HCID 44599974, compound
Reaction equation
[BrH:1].[CH3:2][NH:3][C:4]([C:6]1[CH:7]=[C:8]([O:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([Cl:33])=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=3)=[O:21])=[CH:17][CH:18]=2)[CH:9]=[CH:10][N:11]=1)=[O:5].C(OC(C)C)(C)C>C(O)C>[CH3:2][NH:3][C:4]([C:6]1[CH:7]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([Cl:33])=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:28]=3)=[O:21])=[CH:15][CH:14]=2)[CH:9]=[CH:10][N:11]=1)=[O:5].[BrH:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Aqueous hydrogen bromide (15 mL) was added to a reaction vessel containing sorafenib free base (3.0 g) and the reaction mixture was stirred for about 5 minutes. The temperature was raised to about 70° C. The reaction mixture was stirred for about 2 hours. The solid was precipitated out. The reaction mixture was concentrated and purified by adding toluene (3×15 mL) and concentrated to obtain a solid. Ethanol (2 mL) was added. The reaction mixture was stirred for about 5 minutes followed by the addition of diisopropyl ether (5 mL). The solid was filtered and dried at about 50° C. for about 12 hours to obtain sorafenib hydrobromide.
Workup
- stirringThe reaction mixture was stirred for about 2 hours
- customThe solid was precipitated out
- concentrationThe reaction mixture was concentrated
- custompurified
- additionby adding toluene (3×15 mL)
- concentrationconcentrated
- customto obtain a solid
- stirringThe reaction mixture was stirred for about 5 minutes
- filtrationThe solid was filtered
- customdried at about 50° C. for about 12 hours
Sources & evidence
- ORD record
- ord-ba6fcf30bce24f009ff6a277966f5c76
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614329B2
Reaction notes
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