Methyl Isocyanate → N-methyl-N'-(3-(octahydroindolizin-7-yl)-1H-indol-5-yl)urea

HRID 363334노트

반응식

HRID 363334 반응식
[CH3:1][N:2]=[C:3]=[O:4].[CH2:5]1[CH:13]2[N:8]([CH2:9][CH2:10][CH:11]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([NH2:23])[CH:21]=4)[NH:16][CH:15]=3)[CH2:12]2)[CH2:7][CH2:6]1>CN(C)C=O>[CH3:1][NH:2][C:3]([NH:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:11]1[CH2:12][CH:13]2[N:8]([CH2:7][CH2:6][CH2:5]2)[CH2:9][CH2:10]1)=[O:4]

참가 물질

4

반응물 2

HCID 12228Methyl IsocyanateHCID 153897613-(Octahydroindolizin-7-yl)-5-amino-1H-indole

생성물 1

HCID 44214635N-methyl-N'-(3-(octahydroindolizin-7-yl)-1H-indol-5-yl)urea수율 55.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The methylisocyanate (220 mg, 3.9 mmol) was added to a solution of 3-(octahydroindolizin-7-yl)-5-amino-1H-indole (500 mg, 1.95 mmol) in 10 ml of dimethylformamide. The reaction was allowed to stir for 72 hours. TLC indicated the reaction was complete so the reaction was concentrated to give a purple gum. This material was chromatographed on a short FLORISIL™ column using 20% methanol in methylene chloride (ammonium hydroxide) as solvent to give 340 mg of a white foam. The white foam was recrystallized from methanol/ethyl acetate to give 165 mg of product. (27.1%).

후처리

  1. concentrationwas concentrated
  2. customto give a purple gum
  3. customThis material was chromatographed on a short FLORISIL™ column

출처 및 근거

ORD 기록
ord-8c71a29d084146508f997148f0da02f6
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874427

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