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1-(3-Indolyl)-2-(methylamino)ethanol → HCID 10311734, Verbindung

HRID 982724
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 982724
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[S:19][C:18]([CH2:20]Cl)=[CH:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH:34]([OH:38])[CH2:35][NH:36][CH3:37])=[CH:26]1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[S:19][C:18]([CH2:20][N:36]([CH2:35][CH:34]([OH:38])[C:27]4[C:28]5[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=5)[NH:25][CH:26]=4)[CH3:37])=[CH:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 343191-(3-Indolyl)-2-(methylamino)ethanolHCID 81531DiisopropylethylamineHCID 22563229N-(4-chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Produkt 1

HCID 10311734HCID 10311734, VerbindungAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.26 mmol), 1-(1H-indol-3-yl)-2-(methylamino)ethanol (Khim.-Farm. Zh. 1970, 4, 5-9)(75 mg, 0.39 mmol) and diisopropylethylamine (180 μL, 1.04 mmol) in dry DMF (5 mL) was heated to 60° C., becoming a solution. The reaction was stirred for 5 hours at that temperature. After cooling to room temperature, the solution was diluted with water (15 mL). The resulting milky suspension was stirred vigorously for 30 minutes, and then left standing overnight in the refrigerator. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving a white solid. Recrystallization from acetonitrile/water (dissolved with warming 5 mL of acetonitrile, then cooled to 0° C. and then diluted with 3 mL of water, left overnight) gave the title compound (59 mg) as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. stirringThe resulting milky suspension was stirred vigorously for 30 minutes
  3. waitleft
  4. waitstanding overnight in the refrigerator
  5. filtrationThe mixture was filtered
  6. washthe collected solid was washed with water
  7. customdried in vacuo
  8. customleaving a white solid
  9. customRecrystallization from acetonitrile/water (
  10. dissolutiondissolved
  11. temperaturewith warming 5 mL of acetonitrile
  12. temperaturecooled to 0° C.
  13. additiondiluted with 3 mL of water
  14. waitleft overnight)

Quellen und Nachweise

ORD-Eintrag
ord-b88de20f45ee400eb7d50f0d510cb8f5
Quelldatensatz
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06861438B2

Notizen zur Reaktion

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