Pyrrolidine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1858097Notes

Reaction equation

HRID 1858097 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:32])=[C:24]([CH2:27][CH2:28][C:29]([OH:31])=O)[CH:25]=2)[NH:20][C:19](=[O:33])[C:18]=1[C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)[CH2:45][CH2:46][CH2:47][N:48]=[C:49]=NCC.ON1C2C=CC=CC=2N=N1.N1CCCC1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:32])=[C:24]([CH2:27][CH2:28][C:29](=[O:31])[N:48]3[CH2:49][CH2:45][CH2:46][CH2:47]3)[CH:25]=2)[NH:20][C:19](=[O:33])[C:18]=1[C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 538441682-{2-[6-(2-Carboxyethyl)-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 536595522-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-oxo-3-pyrrolidin-1-yl-propyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl esterYield 55%

Procedure

To a solution of 2-{2-[6-(2-carboxyethyl)-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (15 mg in 0.5 mL of dry methylene chloride) was added 8.0 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) followed by 5.2 mg 1-hydroxybenzotriazole (HOBt) and the mixture stirred for 10 minutes. At this time, 9.2 mg of pyrrolidine was added and the reaction allowed to proceed at room temperature. After 40 minutes, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride: 10% ammonium hydroxide in methanol, 95:5; then 90:10) to give the title compound (9 mg).

Workup

  1. customto proceed at room temperature
  2. waitAfter 40 minutes
  3. concentrationthe mixture was concentrated in vacuo
  4. custompurified by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-09208c2a8eb443b8b969f9c65b382b01
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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