Hexane → N-(4-((4R)-4-((tert-butyl(dimethyl)silyl)oxy)-2-pentynoyl)-3-fluorophenyl)pyrazine-2-carboxamide

HRID 13421Notes

Reaction equation

HRID 13421 reaction equation
C([Li])CCC.CCCCCC.[Si:12]([O:19][C@H:20]([CH3:23])[C:21]#[CH:22])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[F:24][C:25]1[CH:26]=[C:27]([NH:37][C:38]([C:40]2[CH:45]=[N:44][CH:43]=[CH:42][N:41]=2)=[O:39])[CH:28]=[CH:29][C:30]=1[C:31](N(OC)C)=[O:32]>O.O1CCCC1>[Si:12]([O:19][C@H:20]([CH3:23])[C:21]#[C:22][C:31]([C:30]1[CH:29]=[CH:28][C:27]([NH:37][C:38]([C:40]2[CH:45]=[N:44][CH:43]=[CH:42][N:41]=2)=[O:39])=[CH:26][C:25]=1[F:24])=[O:32])([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 8058HexaneHCID 11030608(3R)-3-(tert-butyl(dimethyl)silyl)oxy-1-butyneHCID 23145190N-(3-fluoro-4-((N-methoxy-N-methylamino)carbonyl)phenyl)pyrazine-2-carboxamideHCID 178418339Butyllithium

Product 1

HCID 67482789N-(4-((4R)-4-((tert-butyl(dimethyl)silyl)oxy)-2-pentynoyl)-3-fluorophenyl)pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

10.8 ml of n-butyllithium (2.46 M hexane solution was added to a tetrahydrofuran (80 ml) solution of 4.92 g of (3R)-3-(tert-butyl(dimethyl)silyl)oxy-1-butyne at −78° C., and the reaction liquid was stirred at the same temperature for 1 hour. A tetrahydrofuran (60 ml) solution of 2.7 g of N-(3-fluoro-4-((N-methoxy-N-methylamino)carbonyl)phenyl)pyrazine-2-carboxamide was added to it at −78° C., and the reaction liquid was heated up to room temperature and stirred for 2 hours. Water was added to the reaction liquid, extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. 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 yellow solid.

Workup

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringstirred for 2 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. 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-8acbaea14b864803a091b34e77483466
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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