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

HRID 363334Notes

Reaction equation

HRID 363334 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-8c71a29d084146508f997148f0da02f6
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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