Diisobutylamine → {2-[5-diisobutylcarbamoyl-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-ethyl}carbamic acid tert-butyl ester

HRID 1274405Notes

Reaction equation

HRID 1274405 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:22])=O)[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:53]([NH:57][CH2:58][CH:59]([CH3:61])[CH3:60])[CH:54]([CH3:56])[CH3:55]>>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:22])[N:57]([CH2:58][CH:59]([CH3:61])[CH3:60])[CH2:53][CH:54]([CH3:56])[CH3:55])[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 8085DiisobutylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 221206743-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid

Product 1

HCID 54298340{2-[5-diisobutylcarbamoyl-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-ethyl}carbamic acid tert-butyl ester

Procedure

To a solution of 3-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid (200 mg in 12 mL methylene chloride) was added 104 mg 1-hydroxybenzotriazole followed by 118 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and the mixture stirred at room temperature. After 30 minutes, 0.35 mL of diisobutylamine was added and the mixture stirred at room temperature for 14 hours. The reaction was then concentrated in vacuo and purified by flash chromatography on silica gel (hexane:ethyl acetate, 2:1) to give the title compound (230 mg).

Workup

  1. stirringthe mixture stirred at room temperature for 14 hours
  2. concentrationThe reaction was then concentrated in vacuo
  3. custompurified by flash chromatography on silica gel (hexane:ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-3fb7c9def1104f58913f156b686bf643
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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