Methane → HCID 178520748, compound

HRID 1714406Notes

Reaction equation

HRID 1714406 reaction equation
C(S[C:4](=[O:25])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[O:14])[CH2:8][CH2:7]1)C.C.C([SiH](CC)CC)C.CCCCCCC.C([O-])(=O)C>CC(C)=O.C(Cl)Cl.[Pd]>[O:25]=[CH:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[O:14])[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 297Methane2×HCID 12052Triethylsilane2×HCID 86619959Heptane acetateHCID 178477504HCID 178477504, compound

Product 1

HCID 178520748HCID 178520748, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

Trans-{4-[(Quinoline-4-carbonyl)-amino]-cyclohexyl}-thioacetic acid S— ethyl ester (1.87 g, 5 mmol) was solved in acetone/methylene chloride (40/40 mL), 0.8 g of molecular sieves were added to the mixture and the solution was stirred for 0.5 h. Then 0.558 g (1 mmol) of palladium on active charcoal 10% was added followed by 1.25 mL (8 mmol) of triethyl-silane. The reaction was stirred for 1.5 hours at room temperature and additional 0.558 g (1 mmol) of palladium on active charcoal 10% and 1.25 mL (8 mmol) of triethyl-silane were added and the stirring was continued for another hour. The mixture was filtrated through celite and the mother liquid was concentrated to obtain after chromatography using heptane/acetate 1:1 1.1 (37.1 mmol, 70.8% yield) of the final compound. MS (m/e): 297.3 (M+H+)

Workup

  1. addition0.8 g of molecular sieves were added to the mixture
  2. stirringThe reaction was stirred for 1.5 hours at room temperature
  3. waitthe stirring was continued for another hour
  4. filtrationThe mixture was filtrated through celite
  5. concentrationthe mother liquid was concentrated
  6. customto obtain after chromatography

Sources & evidence

ORD record
ord-5dfdf2f12f6d4d73a92cd0e2179ed0d4
Source dataset
uspto-grants-2010_09
Patent number
US07795437B2

Reaction notes

Loading…