Diethylamine → HCID 86753452, compound

HRID 1458373Notes

Reaction equation

HRID 1458373 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)[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]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:63]([NH:65][CH2:66][CH3:67])[CH3:64]>>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:22])[N:65]([CH2:66][CH3:67])[CH2:63][CH3:64])[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:24]=[C:25]([Cl:30])[CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 4

HCID 8021DiethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22100893HCID 22100893, compound

Product 1

HCID 86753452HCID 86753452, compound

Procedure

To a suspension of 3-{2-[tert-butoxycarbonyl-(4-pyridin-3-yl-butyl)amino]ethyl}-2-(3,5-dichlorophenyl)-1H-indole-5-carboxylic acid (63 mg in 6 mL methylene chloride) was added 24.2 mg 1-hydroxybenzotriazole followed by 26.7 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and the mixture stirred at room temperature. After 30 minutes, 0.06 mL of diethylamine was added and the mixture stirred at room temperature for 16 hours. The reaction was then concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (63 mg).

Workup

  1. stirringthe mixture stirred at room temperature for 16 hours
  2. concentrationThe reaction was then concentrated in vacuo
  3. custompurified by flash chromatography on silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-b73c02df92114db7bc9d07fd7819da7b
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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