4-Methylphenyl isocyanate → 3-[4-({[(4-Methylphenyl)amino]carbonyl}amino)phenyl]-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide

HRID 871009노트

반응식

HRID 871009 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([NH2:15])=[O:14])=[C:11]([NH:16][C:17]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[O:18])[S:10][N:9]=2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:34]1([CH3:43])[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][CH:35]=1>CN(C)C=O.CCOC(C)=O>[CH3:43][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[C:12]([C:13]([NH2:15])=[O:14])=[C:11]([NH:16][C:17]([N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])=[O:18])[S:10][N:9]=3)=[CH:6][CH:7]=2)=[O:42])=[CH:36][CH:35]=1

참가 물질

6

반응물 3

HCID 693254-Methylphenyl isocyanateHCID 81531DiisopropylethylamineHCID 716216283-(4-Aminophenyl)-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide

생성물 1

HCID 716216293-[4-({[(4-Methylphenyl)amino]carbonyl}amino)phenyl]-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide수율 91.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-(4-aminophenyl)-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide (9.6 g, 0.027 mol), diisopropylethylamine (5.3 g, 0.046 mol) in dimethylformamide (150 mL) at ambient temperature was treated with para-Tolyl isocyanate (4.0 g 0.03 mol) over 20 minute period. The resulting mixture was stirred at ambient temperature for 2 hr. The reaction mixture was concentrated in vacuo to give an off white solid, which was stirred in EtOAc (150 mL), filtered the solid and washed with EtOAc to give the title compound as a white solid (11.8 g, 88%).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give an off white solid, which
  3. filtrationfiltered the solid
  4. washwashed with EtOAc

출처 및 근거

ORD 기록
ord-23fabe61206a439991d8ed5c0f28c8aa
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969583B2

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