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

HRID 363335Notes

Reaction equation

HRID 363335 reaction equation
C[Si](N=C=O)(C)C.[CH2:8]1[CH:16]2[N:11]([CH2:12][CH2:13][CH:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([NH2:26])[CH:24]=4)[NH:19][CH:18]=3)[CH2:15]2)[CH2:10][CH2:9]1.[CH3:27][N:28](C)[CH:29]=[O:30]>>[CH3:27][NH:28][C:29]([NH:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH:14]1[CH2:15][CH:16]2[N:11]([CH2:10][CH2:9][CH2:8]2)[CH2:12][CH2:13]1)=[O:30]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 70696Trimethylsilyl isocyanateHCID 153897613-(Octahydroindolizin-7-yl)-5-amino-1H-indole

Product 1

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

Procedure

The trimethylsilyl isocyanate (288 mg, 2.50 mmol) was added to a solution of 3-(octahydroindolizin-7-yl)-5-amino-1H-indole (322 mg, 1.26 mmol) in 5 ml of dimethylformamide. The reaction was stirred at room temperature for 24 hours. TLC indicated consumption of starting material so the reaction was concentrated to give a purple foam which solidified. This material was chromatographed on a FLUORISIL™ column using 20% methanol in methylene chloride (ammonium hydroxide) as solvent to give 164 mg of product. (43.7%).

Workup

  1. customconsumption of starting material so the reaction
  2. concentrationwas concentrated
  3. customto give a purple foam which
  4. customThis material was chromatographed on a FLUORISIL™ column

Sources & evidence

ORD record
ord-75aa1d6875644420b43044182bd383fa
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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