4-Fluorophenyl isocyanate → N-(2-methylcarbamoyl-5-tert-butylfuryl)-N'-(4-fluorophenyl)urea

HRID 1698910노트

반응식

HRID 1698910 반응식
[CH3:1][NH:2][C:3]([C:5]1[O:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH2:10])=[O:4].[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]([C:5]1[O:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH:10][C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=1)=[O:24])=[O:4]

참가 물질

4

반응물 2

HCID 709554-Fluorophenyl isocyanateHCID 18322380N-methyl-3-amino-5-tert-butyl-2-furancarboxamide

생성물 1

HCID 9923703N-(2-methylcarbamoyl-5-tert-butylfuryl)-N'-(4-fluorophenyl)urea수율 63.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of N-methyl-3-amino-5-tert-butylfuran-2-carboxamide (0.15 g, 0.76 mmol) in anh. toluene (2 mL) at the reflux temp. was slowly added 4-fluorophenyl isocyanate (0.10 g, 0.76 mmol, 1.0 equiv). The resulting solution was allowed to stir at the reflux temp. for 14 h, cooled to room temp., and concentrated under reduced pressure. The residue was purified by flash chromatography (15 g SiO2, gradient from 50% CH2Cl2/hexane to 100% CH2Cl2, then to 20% EtOAc/CH2Cl2) to afford N-(2-methylcarbamoyl-5-tert-butylfuryl)-N′-(4-fluorophenyl)urea (0.16 g, 61%): mp 109-11° C., TLC (30% EtOAc/CH2Cl2) Rf0.21; 1H NMR (CDCl3) δ1.29 (s, 9H), 2.89 (d, J=4.8 Hz, 3H), 6.02 (br q, J=4.8 Hz, 1H), 6.98 (app td, J=16.6, 4.1 Hz, 2H), 7.01 (s, 1H), 7.34-7.39 (m, 2H), 8.05 (br s, 1H), 9.14 (s, 1H); 13C NMR (CDCl3) δ25.5, 28.7 (3C), 33.1, 100.7, 115.6 (d, JC-F=23.2 Hz, 2C), 121.5 (d, JC-F=7.3 Hz, 2C), 128.3, 134.5 (br s), 152.4, 158.9 (d, JC-F=242.9 Hz, 1C), 161.6, 165.8; FAB-LRMS m/z (rel abundance) 334 (M+H, 100%).

후처리

  1. temperaturecooled to room temp.
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (15 g SiO2, gradient from 50% CH2Cl2/hexane to 100% CH2Cl2

출처 및 근거

ORD 기록
ord-ce74755e9c98424e814374a84940b3fe
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06344476B1

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