Diisopropylethylamine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl ester

HRID 1858076Notes

Reaction equation

HRID 1858076 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:22][CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][NH:25]3)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:30]([O-:32])=[O:31].[C:33](=O)([O:41]C1C=CC([N+]([O-])=O)=CC=1)[O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38].C(N(C(C)C)CC)(C)C>>[CH3:38][Si:37]([CH3:40])([CH3:39])[CH2:36][CH2:35][O:34][C:33]([N:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]1[CH2:23][CH2:22][O:21][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([N+:30]([O-:32])=[O:31])[CH:4]=2)[NH:9][C:8](=[O:12])[C:7]=1[C:13]1[CH:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)=[O:41]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 30861164-Nitrophenyl 2-(trimethylsilyl)ethyl carbonateHCID 221245137-chloro-3-(3,5-dimethylphenyl)-6-nitro-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one

Product 1

HCID 539966322-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid 2-trimethylsilanylethyl esterYield 69.5%

Procedure

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-6-nitro-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-one (200 mg in 5 mL dicloroethane) was added 136 mg of 2-(trimethylsilyl)ethyl 4-nitrophenyl carbonate followed by 0.092 mL diisopropylethylamine and the mixture heated to reflux. After 20 hours, the reaction was cooled to room temperature, concentrated in vacuo and purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:1) to give the title compound (183 mg.)

Workup

  1. temperaturethe mixture heated to reflux
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography on silica gel (ethyl acetate:hexane, 1:1)

Sources & evidence

ORD record
ord-0ea4e2d319264667830ec9f4f8c2e71f
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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