Triethylamine → HCID 54229053, compound

HRID 1419165Notes

Reaction equation

HRID 1419165 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15]CN1C.Cl[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:22]([C:28]#[N:29])=[CH:21][N:20]=1.[CH2:30]([N:32](CC)[CH2:33]C)C.C(Cl)Cl.CO.[OH-].[NH4+]>C(O)C>[C:28]([C:22]1[CH:23]=[C:24]([N+:25]([O-:27])=[O:26])[C:19]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH2:11][CH:12]2[CH2:16][CH2:15][N:32]([CH3:33])[CH2:30]2)=[N:20][CH:21]=1)#[N:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indoleHCID 185096266-chloro-5-nitronicotinonitrileHCID 21896990Dichloromethane methanol ammonium hydroxide

Product 1

HCID 54229053HCID 54229053, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and 2-chloro-5-cyano-3-nitropyridine were used. Triethylamine was used as base, absolute ethanol was used as solvent, and the reaction was heated at reflux for 2 hours. Column chromatography using 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide] afforded the title compound (53%) as a red foam: Rf =0.2 in 20% methanol in methylene chloride; 13C NMR (CD3OD) δ 158.3, 140.3, 136.5, 130.0, 128.4, 125.9, 122.2, 120.4, 115.2, 112.8, 111.1, 98.4, 70.1, 57.9, 40.4, 31.3, 28.2, 22.4; HRMS calculated for C20H20N6O2 376.1650, found 376.1653.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 2 hours

Sources & evidence

ORD record
ord-9304f200b96744dbaf3ecbe18c75650d
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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