HCID 178418361, compound → HCID 178436690, compound

HRID 2053766Notes

Reaction equation

HRID 2053766 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[NH:6][C:7]([CH:9]([NH:11][C:12](=[O:28])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[O:20])=[C:15]([C:26]#[CH:27])[CH:14]=3)[CH3:10])=[N:8][C:4]=2[CH:3]=1.[H][H]>O1CCOCC1.O.[Pt]>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[NH:6][C:7]([CH:9]([NH:11][C:12](=[O:28])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)=[O:20])=[C:15]([CH2:26][CH3:27])[CH:14]=3)[CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178436689HCID 178436689, compound

Product 1

HCID 178436690HCID 178436690, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

60 mg (0.143 mmol) of N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-3-ethynyl-4-(pyrrolidin-1-ylcarbonyl)benzamide is dissolved in 6.0 mL dioxane/water (1:1), combined with 8.0 mg platinum/activated charcoal and hydrogenated for 7 hours with hydrogen (3 bar). Then the catalyst is filtered off and the solvent is distilled off. Yield: 99%; Rf value: 0.15 (Reversed-phase-8; methanol/5%-NaCl solution=3:2); C23H25ClN4O2 (424.93); mass spectrum: (M−H)-=423/425 (chlorine isotope) and (M+H)+=425/427 (chlorine isotope).

Workup

  1. filtrationThen the catalyst is filtered off
  2. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-a2e1fbe12e9f48ba805ff8336e2f2980
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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