[2-(4-Benzyloxyphenyl)-ethyl]-carbamic acid 4-nitrophenyl ester → 1-[2-(4-benzyloxyphenyl)ethyl]-3-{2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}urea

HRID 1292404Notes

Reaction equation

HRID 1292404 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH2:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[N+](C1C=CC([O:30][C:31](=O)[NH:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:37][CH:36]=2)=CC=1)([O-])=O>>[CH2:42]([O:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][CH2:33][NH:32][C:31]([NH:20][CH2:19][CH2:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=2)=[O:30])=[CH:40][CH:39]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

3

Reactant 2

HCID 11429281[2-(4-Benzyloxyphenyl)-ethyl]-carbamic acid 4-nitrophenyl esterHCID 221009192-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamine

Product 1

HCID 189142771-[2-(4-benzyloxyphenyl)ethyl]-3-{2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}ureaYield 95.6%

Procedure

To a solution of 2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamine (EXAMPLE 2 Step D, 39 mg in 1 mL dry methanol) was added 64 mg [2-(4-benzyloxyphenyl)-ethyl]-carbamic acid 4-nitrophenyl ester and the mixture stirred at room temperature. After 24 hours, the mixture was concentrated in vacuo and the residue re-solvated in ethyl acetate. This was washed with saturated aqueous potassium carbonate (3×) and brine, dried over sodium sulfate and purified by flash chromatography on silica gel (hexane:ethyl acetate, 5:4; then 1:1) to give the title compound (73 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. washThis was washed with saturated aqueous potassium carbonate (3×) and brine
  3. dry with materialdried over sodium sulfate
  4. custompurified by flash chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-45c7845f7acc49a5a87deeca9bbb99aa
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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