反応 #58864

反応方程式

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

収率 16.0%

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

収率 16.0%

溶媒

CH2Cl2

CH2Cl2

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   workup.STIRRINGstirred for 20 min
2. 2
   その他to come to room temperature
3. 3
   workup.STIRRINGstirred for 2 h at room temperature
4. 4
   その他quenched with aqueous NH4Cl
5. 5
   抽出extracted with CH2Cl2
6. 6
   乾燥The combined extracts are dried over MgSO4
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The resultant residue is purified by SCX cartridge and preparative HPLC

実験手順

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

出典