Réaction #58864

Équation de réaction

diethyl zinc

CF3CO2H

CH2I2

2-amino-5-[4-(difluoromethoxy)phenyl]-5-{3-[(1E)-3-methoxyprop-1-en-1-yl]phenyl}-3-methyl-3,5-dihydro-4H-imidazol-4-one

→

title compound

Rendement 16.0%

2-Amino-5-[4-(difluoromethoxy)phenyl]-5-{3-[2-(methoxymethyl)cyclopropyl]phenyl}-3-methyl-3,5-dihydro-4H-imidazol-4-one

Rendement 16.0%

Solvants

CH2Cl2

CH2Cl2

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred for 20 min
2. 2
   Autreto come to room temperature
3. 3
   workup.STIRRINGstirred for 2 h at room temperature
4. 4
   Autrequenched with aqueous NH4Cl
5. 5
   Extractionextracted with CH2Cl2
6. 6
   SéchageThe combined extracts are dried over MgSO4
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutreThe resultant residue is purified by SCX cartridge and preparative HPLC

Mode opératoire

A 1M solution of diethyl zinc (4.92 ml, 4.92 mmol) in dry CH2Cl2 at 0° C. is treated very slowly with a solution of CF3CO2H (0.56 g, 4.92 mmol) in dry CH2Cl2, stirred for 20 min, treated dropwise with a solution of CH2I2 (0.66 g, 2.46 mmol) in dry CH2Cl2, stirred for 20 min, treated with a solution of 2-amino-5-[4-(difluoromethoxy)phenyl]-5-{3-[(1E)-3-methoxyprop-1-en-1-yl]phenyl}-3-methyl-3,5-dihydro-4H-imidazol-4-one (197 mg, 0.492 mmol) in dry CH2Cl2, allowed to come to room temperature, stirred for 2 h at room temperature, quenched with aqueous NH4Cl and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by SCX cartridge and preparative HPLC to give the title compound as a white solid, 32 mg (16% yield), identified by NMR and mass spectral analyses. (1H-NMR 300 MHz, DMSO): 7.46(d, 2H); 7.24-7.13(m, 3H); 7.16(t, 1H); 7.10(d, 2H); 6.88(m, 1H); 6.64(s br, 2H); 3.44-3.34(m, 2H); 3.24(m, 1H); 3.23(s, 3H); 2.97(s, 3H); 1.76(m, 1H); 0.90-0.76(m, 2H). MS [M+H]+ 416.1

Source