4-Methylmorpholine → HCID 57742593, Verbindung

HRID 911897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911897
[Br:1][C:2]1[CH:3]=[C:4]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:20][CH3:21])([CH3:19])[C:16](O)=[O:17])[N:13]=2)=[N:6][CH:7]=1.C[N:30]1[CH2:35][CH2:34]O[CH2:32][CH2:31]1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.N1CCCC1>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:20][CH3:21])([CH3:19])[C:16]([N:30]3[CH2:35][CH2:34][CH2:32][CH2:31]3)=[O:17])[N:13]=2)=[N:6][CH:7]=1

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 57742924HCID 57742924, Verbindung

Produkt 1

HCID 57742593HCID 57742593, VerbindungAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a 20 mL scintillation vial, 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)-2-methoxy-2-methylpropanoic acid (0.087 g, 0.187 mmol) was dissolved in CH2Cl2 (5 mL) and DMF (2 mL) and N-methylmorpholine (0.031 mL, 0.281 mmol), followed by addition of 1-hydroxybenzotriazole. The mixture was cooled to 0° C. and EDCI (0.0467 g, 0.244 mmol) was added. The resulting mixture was agitated for 30 minutes and pyrrolidine (0.020 g, 0.28 mmol) was added. The mixture was then agitated overnight, diluted with 50 mL of CH2Cl2 and washed with citric acid solution and sodium bicarbonate solution, dried and evaporated to give crude product which was purified by chromatography on silica gel, eluting with 50-70% ethyl acetate/Hexane, to provide the title compound (0.079 g, 79% yield) as white solid. 1H NMR (DMSO-d6 δ 1.23 (s, 3H), 1.66-1.80 (m, 4H), 3.03-3.63 (m, 9H), 7.01 (m, 1H), 7.16-7.46 (m, 7H), 8.25 (s, 1H).

Aufarbeitung

  1. stirringThe mixture was then agitated overnight
  2. washwashed with citric acid solution and sodium bicarbonate solution
  3. customdried
  4. customevaporated
  5. customto give crude product which
  6. customwas purified by chromatography on silica gel
  7. washeluting with 50-70% ethyl acetate/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-17f9802b5297499f9635c4dd04d29fd8
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022223B2

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