Diisopropylethylamine → 2-{[[2-(1,3-Benzodioxol-5-yl)-2-hydroxyethyl](methyl)amino]methyl}-N-(4-chlorobenzyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 982726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 982726
[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.[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([CH:34]([OH:38])[CH2:35][NH:36][CH3:37])=[CH:33][C:28]=2[O:27][CH2:26]1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([CH:34]([OH:38])[CH2:35][N:36]([CH2:20][C:18]3[S:19][C:12]4[C:11](=[O:22])[C:10]([C:8]([NH:7][CH2:6][C:5]5[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=5)=[O:9])=[CH:15][N:14]([CH3:16])[C:13]=4[CH:17]=3)[CH3:37])=[CH:33][C:28]=2[O:27][CH2:26]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 125605461-(1,3-Dioxaindan-5-yl)-2-(methylamino)ethan-1-olHCID 22563229N-(4-chlorobenzyl)-2-(chloromethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Produkt 1

HCID 101749082-{[[2-(1,3-Benzodioxol-5-yl)-2-hydroxyethyl](methyl)amino]methyl}-N-(4-chlorobenzyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 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 (80 mg, 0.21 mmol), 1-(1,3-benzodioxol-5-yl)-2-(methylamino)ethanol (Journal of Organometallic Chemistry, 1998, 339, 267-75) (62 mg, 0.32 mmol) and diisopropylethylamine (67 μL, 0.38 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 3 mL of acetonitrile, then cooled to 0° C. and then diluted with 2 mL of water, left overnight) gave the title compound (74 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 3 mL of acetonitrile
  12. temperaturecooled to 0° C.
  13. additiondiluted with 2 mL of water
  14. waitleft overnight)

Quellen und Nachweise

ORD-Eintrag
ord-352ce983dfa94acdae1ab187f8cd40ad
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861438B2

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