(4-Nitrophenyl)acetic acid → HCID 18914244, compound

HRID 1292377Notes

Reaction equation

HRID 1292377 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:36][CH2:37][CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[NH:41][C:40]=1[C:48]1[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[C:50]([O:56][CH3:57])[CH:49]=1>>[CH3:57][O:56][C:50]1[CH:49]=[C:48]([C:40]2[NH:41][C:42]3[C:47]([C:39]=2[CH2:38][CH2:37][NH:36][C:11](=[O:13])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:53]=[CH:52][C:51]=1[O:54][CH3:55]

Participants

5

Reactant 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 368016595426-76-9

Product 1

HCID 18914244HCID 18914244, compoundYield 45.7%

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-nitrophenylacetic acid (100 mg in 2.5 mL N,N-dimethylformamide) was added 1-hydroxybenzotriazole (90 mg) and the mixture cooled to 0° C. After 10 minutes, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (148 mg) was added. The mixture was warmed to room temperature and 3-(2-aminoethyl)-2-(3,4-dimethoxyphenyl)indole (316 mg) was added. After 17 hours the reaction was quenched by the addition of water and extracted with ethyl acetate. The organic portion was washed with water, 0.5M sodium bisulfate and brine, dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel (hexane:ethyl acetate, 1:2) gave the title compound (116 mg).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. customAfter 17 hours the reaction was quenched by the addition of water
  3. extractionextracted with ethyl acetate
  4. washThe organic portion was washed with water, 0.5M sodium bisulfate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (hexane:ethyl acetate, 1:2)

Sources & evidence

ORD record
ord-fbf5ba37b9e14a8a9bbc2118b2213ad5
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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