5-Amino-1-(2-pyrrolidin-1-ylethyl)indole → HCID 57845822, compound

HRID 735095Notes

Reaction equation

HRID 735095 reaction equation
Cl[CH2:2][Cl:3].[CH3:4][OH:5].N.[NH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][CH2:18][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH:12]=[CH:11]2>ClC1C=C(Cl)C=CC=1C#CC(O)=O.C1COCC1>[N:19]1([CH2:18][CH2:17][N:13]2[C:14]3[C:10](=[CH:9][C:8]([NH:7][C:4](=[O:5])[C:15]#[C:14][C:10]4[CH:11]=[CH:12][C:2]([Cl:3])=[CH:8][CH:9]=4)=[CH:16][CH:15]=3)[CH:11]=[CH:12]2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 113905745-Amino-1-(2-pyrrolidin-1-ylethyl)indoleHCID 21584172Ammonia methanol dichloromethane

Product 1

HCID 57845822HCID 57845822, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2285093-(2,4-dichlorophenyl)prop-2-ynoic acidSolvent

Procedure

Prepared analogously to Example 3.1.e. from 5-amino-1-(2-pyrrolidin-1-ylethyl)-1H-indole and (2,4-dichlorophenyl)propynoic acid in THF as solvent. Yield: 133 mg (31.2% of theory); C23H21Cl2N3O (M=426.34); melting point: 127° C.-129° C.; calc.: molecular ion peak (M+H)+: 426/428/430; found: molecular ion peak (M+H)+: 426/428/430; Rf value: 0.4 (silica gel, dichloromethane/methanol/ammonia (90:10:1)).

Workup

  1. customPrepared analogously to Example 3.1.e

Sources & evidence

ORD record
ord-c7e4f14e65e8419dba77c160f29bc7e6
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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