Tert-butyl({5-[5-chloro-3-fluoro-2-(2-methyl-2h-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)carbamate → ({5-[5-Chloro-3-fluoro-2-(2-methyl-2h-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)amine
Reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([F:23])[C:17]=2[C:24]2[N:25]=[N:26][N:27]([CH3:29])[N:28]=2)=[CH:11][N:10]=1)(C)(C)C>CCOC(C)=O>[Cl:22][C:20]1[CH:19]=[C:18]([F:23])[C:17]([C:24]2[N:25]=[N:26][N:27]([CH3:29])[N:28]=2)=[C:16]([C:12]2[CH:13]=[C:14]([F:15])[C:9]([CH2:8][NH2:7])=[N:10][CH:11]=2)[CH:21]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The above carbamate was dissolved in 50 mL of dry EtOAc. Anhydrous HCl gas was then bubbled through the solution for 3 minutes. The reaction was stirred vigorously for one hour. The reaction mixture was slowly neutralized with a saturated aqueous sodium bicarbonate solution. The mixture was partitioned between water and EtOAc. The organic layer was washed with water and brine prior to drying over sodium sulfate. The extracts were filtered, concentrated, and purified by chromatography on silica gel eluting with 0-20% MeOH in dichloromethane to provide ({5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)amine.
Workup
- customAnhydrous HCl gas was then bubbled through the solution for 3 minutes
- customThe mixture was partitioned between water and EtOAc
- washThe organic layer was washed with water and brine
- dry with materialto drying over sodium sulfate
- filtrationThe extracts were filtered
- concentrationconcentrated
- custompurified by chromatography on silica gel eluting with 0-20% MeOH in dichloromethane
Sources & evidence
- ORD record
- ord-8e5198affd544743acdae1d9e73d438b
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816380B2
Reaction notes
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