Lithium hydroxide, monohydrate → (E)-N-indan-1-yl-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamide

HRID 1362591Notes

Reaction equation

HRID 1362591 reaction equation
O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1)[CH:9]=O.C(OP([CH2:28][C:29](=[O:40])[NH:30][CH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32]1)(=O)OCC)C>C1COCC1>[CH:31]1([NH:30][C:29](=[O:40])/[CH:28]=[CH:9]/[C:8]2[CH:11]=[CH:12][C:13]([N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]3)=[C:6]([O:5][CH3:4])[CH:7]=2)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86602465(Indan-1-ylcarbamoylmethyl)phosphonic acid diethyl ester

Product 1

HCID 59170837(E)-N-indan-1-yl-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamideYield 36.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (9 mg) was added to a THF (2 mL) solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (21 mg) and indan-1-ylcarbamoylmethylphosphonic acid diethyl ester (30 mg) obtained above, and the reaction solution was agitated at room temperature overnight. After the reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: hexane-ethyl acetate system), and 13 mg of the title compound was obtained.

Workup

  1. customobtained above, and the reaction solution
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-03f93050bfc24be591306470faa2ea65
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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