HCID 68455943, compound → HCID 68455989, compound

HRID 2358438Notes

Reaction equation

HRID 2358438 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:35])[NH:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[C:18]([C:27]#[C:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:17]=2)[CH3:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:35])[NH:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[C:18]([CH:27]=[CH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:17]=2)[CH3:15])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 68455943HCID 68455943, compound

Product 1

HCID 68455989HCID 68455989, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

N-(4-{1-[3-(4-tert-Butyl-phenyl)-ureido]-ethyl}-2-phenylethynylphenyl)-methanesulfonamide (50 mg, 0.102 mmol, 1 eq.) and palladium on calcium carbonate, poisoned with lead (Lindlar catalyst) were added in methanol. The reaction mixture stirred 12 hrs under H2 atmosphere. The reaction mixture was filtered with celite pad. The filterate was concentrated in vacuo. The residue was purified with column chromatography (n-Hx:EA=2:1) to yield title compound (16 mg, 32%).

Workup

  1. filtrationThe reaction mixture was filtered with celite pad
  2. concentrationThe filterate was concentrated in vacuo
  3. customThe residue was purified with column chromatography (n-Hx:EA=2:1)

Sources & evidence

ORD record
ord-ad0c38f166004efeb368192b66db3802
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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