Ethyl Acrylate → HCID 59146183, compound

HRID 1512791Notes

Reaction equation

HRID 1512791 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:25]=[CH:26][CH:27]=[C:28]4[C:32]=3[NH:31][CH:30]=[C:29]4[CH2:33][CH2:34][NH2:35])[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]>ClCCl.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3]>[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:25]=[CH:26][CH:27]=[C:28]4[C:32]=3[NH:31][CH:30]=[C:29]4[CH2:33][CH2:34][NH:35][CH2:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 8821Ethyl AcrylateHCID 59146144HCID 59146144, compound

Product 1

HCID 59146183HCID 59146183, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6344DichloromethaneSolvent

Procedure

Ethyl acrylate (100 mg) and Sc(OTf)3 (5 mg) were added to the solution of 2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]ethanamine (D84) (530 mg) in dichloromethane (3 mL). The resulting reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated and the residue was purified by Mass Directed Auto Prep to afford ethyl N-{2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]ethyl}-β-alaninate (D85) (186 mg) as a yellow solid. MS (ES): C26H29ClN4O4 requires 496; found 497.2 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by Mass Directed Auto Prep

Sources & evidence

ORD record
ord-a7c0000c67094bf7bc66780480bf90cd
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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