Urea → 3-[1-Benzyl-3-(4-cyano-phenyl)-ureidomethyl]-benzoic acid methyl ester

HRID 418358

반응식

HRID 418358 반응식
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=1.[C:20]([C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1)#[N:21].NC(N)=O>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:29]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([C:20]#[N:21])=[CH:23][CH:24]=2)=[O:30])[CH:5]=1

참가 물질

6

반응물 3

HCID 1176UreaHCID 1703804-Cyanophenyl isocyanateHCID 591908593-(Benzylamino-methyl)-benzoic acid methyl ester

생성물 1

HCID 591908863-[1-Benzyl-3-(4-cyano-phenyl)-ureidomethyl]-benzoic acid methyl ester수율 34.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Dissolved 3-(benzylamino-methyl)-benzoic acid methyl ester (197 mg, 0.77 mmol) in 5 mL of DMF. To this was added 4-cyanophenyl isocyanate (112 mg, 0.78 mmol). The mixture stirred for 48. LC-MS analysis indicated the desired urea. The mixture was diluted with 100 mL EtOAc, washed with 3×50 mL of H2O and 1×20 mL of brine. The organic phase was dried with MgSO4, filtered and concentrated. The resulting residue was applied to a SiO2 prep plate and eluted with 50% EtOAc/hexanes to give two fractions-one clear band and a tail. LC-MS analysis indicated both band and tail were composed of the product. Both fractions were combined to give 105.7 mg of 3-[1-benzyl-3-(4-cyano-phenyl)-ureidomethyl]-benzoic acid methyl ester.

후처리

  1. washwashed with 3×50 mL of H2O and 1×20 mL of brine
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluted with 50% EtOAc/hexanes
  6. customto give two fractions-one clear band

출처 및 근거

ORD 기록
ord-1dd697f7b4654f87b81ba998a32e8e35
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093266B2

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