2-Cyclohexylethylamine → 1-[6-Chloro-5-[[(2-cyclohexylethyl)amino]carbonyl]-2-quinolinyl]-4-piperidinecarboxylic acid ethyl ester

HRID 2217878Notes

Reaction equation

HRID 2217878 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH:6]=[CH:5][C:4]=2[C:3]=1[C:23](O)=[O:24].[CH:26]1([CH2:32][CH2:33][NH2:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>>[CH2:21]([O:20][C:18]([CH:15]1[CH2:16][CH2:17][N:12]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[C:3]=3[C:23]([NH:34][CH2:33][CH2:32][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:24])[N:8]=2)[CH2:13][CH2:14]1)=[O:19])[CH3:22]

Participants

3

Reactant 2

HCID 205092-CyclohexylethylamineHCID 688089486-Chloro-2-[4-(ethoxycarbonyl)-1-piperidinyl]-5-quinolinecarboxylic acid

Product 1

HCID 688089401-[6-Chloro-5-[[(2-cyclohexylethyl)amino]carbonyl]-2-quinolinyl]-4-piperidinecarboxylic acid ethyl esterYield 70.8%

Procedure

Prepared according to the method of example 4(a), using 6-chloro-2-[4-(ethoxycarbonyl)-1-piperidinyl]-5-quinolinecarboxylic acid (example 76(c)) (217 mg) and cyclohexaneethanamine (277 mg). Purification (SiO2, methanol:dichloromethane 1:99 as eluant) gave the title compound as a solid (200 mg).

Workup

  1. customPrepared
  2. customPurification (SiO2, methanol:dichloromethane 1:99 as eluant)

Sources & evidence

ORD record
ord-086e6816f30d47779ad9397533ee4e27
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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