1-Hydroxybenzotriazole → HCID 22100913, compound

HRID 1458336Notes

Reaction equation

HRID 1458336 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:37][O:38][C:39]1[CH:40]=[C:41]([C:47]2[NH:48][C:49]3[C:54]([C:55]=2[CH2:56][CH2:57][NH2:58])=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:42]=[CH:43][C:44]=1[O:45][CH3:46]>>[CH3:37][O:38][C:39]1[CH:40]=[C:41]([C:47]2[NH:48][C:49]3[C:54]([C:55]=2[CH2:56][CH2:57][NH:58][C:12](=[O:14])[CH2:11][CH2:10][C:6]2[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=2)[NH:1][CH:2]=[CH:3]4)=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:42]=[CH:43][C:44]=1[O:45][CH3:46]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 368016595426-76-9HCID 221008923-(1H-Indol-5-yl)propanoic acid

Product 1

HCID 22100913HCID 22100913, compoundYield 89.8%

Procedure

To a solution of 3-(1H-indol-5-yl)propionic acid (50 mg in 2.5 mL N,N-dimethylformamide) at 0° C. was added 43 mg 1-hydroxy-benzotriazole followed by 71 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and the mixture allowed to warm to room temperature. After 23 minutes, 155 mg of 2-[2-(3,4-dimethoxyphenyl)-1H-indol-3-yl]-ethylamine was added and the mixture stirred at room temperature for an additional hour. The reaction was then quenched by the addition of water and the mixture extracted with ethyl acetate. The combined organics were washed with water and brine, dried over sodium sulfate and the concentrated oil purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (111 mg).

Workup

  1. customThe reaction was then quenched by the addition of water
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe combined organics were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customthe concentrated oil purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-d2998862ff69448f86980a547ab71ab5
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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