Methanol → 1-[2-(4-Cyano-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea

HRID 1860225Notes

Reaction equation

HRID 1860225 reaction equation
CO[C:3](=[O:19])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:20][NH:21][C:22]([NH2:24])=[O:23].C[O-].[Mg+2].C[O-].CO>>[C:17]([C:14]1[CH:13]=[CH:12][C:11]([CH:4]([CH2:5][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[C:3]([NH:24][C:22]([NH:21][CH3:20])=[O:23])=[O:19])=[CH:16][CH:15]=1)#[N:18]

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 544451542-(4-Cyano-phenyl)-3-cyclopentyl-propionic acid methyl ester

Product 1

HCID 186266271-[2-(4-Cyano-phenyl)-3-cyclopentyl-propionyl]-3-methyl-ureaYield 16.3%

Procedure

A mixture of 2-(4-cyano-phenyl)-3-cyclopentyl-propionic acid methyl ester (257 mg, 1.0 mmol) and methyl urea (148 mg, 2.0 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 2.0 mL, 1.40 mmol) was heated to reflux for 48 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 70/30 ethyl acetate/hexanes) afforded 1-[2-(4-cyano-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea (48.8 mg, 16.3%) as a white solid: mp 61-65° C.; FAB-HRMS m/e calcd for C17H21N3O2 (M+H)+300.1712 found 300.1722.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-0dd7c3fc67da42788ceda19a4822609e
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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