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Diisopropylcarbodiimide → 1-(4-Methoxynaphthalene-1-sulfonyl)-2,3-dihydro-1H-indole-3-carboxylic Acid [2-(1-methyl-pyrrolidin-2-yl)-ethyl]amide

HRID 1174518
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1174518
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([S:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]([C:25]([OH:27])=O)[CH2:17]2)(=[O:15])=[O:14])=[CH:5][CH:4]=1.ON1C2C=CC=CC=2N=N1.CC(C)N=C=NC(C)C.[CH3:47][N:48]1[CH2:52][CH2:51][CH2:50][CH:49]1[CH2:53][CH2:54][NH2:55]>ClCCl.O>[CH3:47][N:48]1[CH2:52][CH2:51][CH2:50][CH:49]1[CH2:53][CH2:54][NH:55][C:25]([CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([S:13]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:14])=[O:15])[CH2:17]1)=[O:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 687698721-(4-methoxynaphthalene-1-sulfonyl)-2,3-dihydro-1H-indole-3-carboxylic Acid

Produkt 1

HCID 98703421-(4-Methoxynaphthalene-1-sulfonyl)-2,3-dihydro-1H-indole-3-carboxylic Acid [2-(1-methyl-pyrrolidin-2-yl)-ethyl]amide
Ausbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(4-methoxynaphthalene-1-sulfonyl)-2,3-dihydro-1H-indole-3-carboxylic acid (C) (900 mg, 2.35 mmol) in dichloromethane (20 cm3) was added 1-hydroxybenzotriazole (HOBT, 0.48 g, 3.53 mmol) and 1,3-diisopropylcarbodidiimide (DIC, 0.55 cm3, 3.53 mmol). This was left to stir at room temperature for 5 min, before adding 2-(1-methyl-pyrrolidin-2-yl)-ethylamine (0.342 cm3, 2.35 mmol). The reaction was stirred for 16 h at room temperature before water (60 cm3) was added followed by dichloromethane (60 cm3). The resulting mixture was then shaken and the organic layer was washed with water (40 cm3), saturated aqueous sodium bicarbonate solution (40 cm3), water again (40 cm3) and then saturated aqueous sodium chloride solution (50 cm3) before the organic portion was dried over sodium sulfate, It was then evaporated under reduced pressure to afford the title compound (1) (800 mg, 1.62 mmol, 69%), positive ion ESI (M+H)+ 494.6.

Aufarbeitung

  1. waitThis was left
  2. additionwas added
  3. stirringThe resulting mixture was then shaken
  4. washthe organic layer was washed with water (40 cm3), saturated aqueous sodium bicarbonate solution (40 cm3), water again (40 cm3)
  5. dry with materialsaturated aqueous sodium chloride solution (50 cm3) before the organic portion was dried over sodium sulfate, It
  6. customwas then evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4ef310abf07b47d4a52042046521f4af
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07838518B2

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