N-(4-((4R)-4-((tert-butyl(dimethyl)silyl)oxy)-2-pentynoyl)-3-fluorophenyl)pyrazine-2-carboxamide → N-(4-((4R)-4-((tert-butyl(dimethyl)silyl)oxy)-pentanoyl)-3-fluorophenyl)pyrazine-2-carboxamide
Reaction equation
[Si:1]([O:8][C@H:9]([CH3:30])[C:10]#[C:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[CH:28]=[N:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[CH:16][C:15]=1[F:29])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>[C].[Pd].O1CCCC1.C(O)C>[Si:1]([O:8][C@H:9]([CH3:30])[CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[CH:28]=[N:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[CH:16][C:15]=1[F:29])=[O:13])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
100 mg of 10% palladium-carbon catalyst was added to a solution of 513 mg of N-(4-((4R)-4-((tert-butyl(dimethyl)silyl)oxy)-2-pentynoyl)-3-fluorophenyl)pyrazine-2-carboxamide in 5 ml of tetrahydrofuran and 20 ml of ethanol, and the reaction liquid was stirred in a hydrogen atmosphere for 1.5 hours. The catalyst was removed through filtration, the solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 1/1) to obtain the entitled compound as a pale yellow solid.
Workup
- customthe reaction liquid
- customThe catalyst was removed through filtration
- customthe solvent was evaporated away under reduced pressure
- customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 1/1)
Sources & evidence
- ORD record
- ord-b71af555d8d843fda038a05b0f47f53d
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728025B2
Reaction notes
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