Chloroacetaldehyde → 4-[3-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-ol

HRID 2075665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075665
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([S:18][C:19]3[CH:20]=[C:21]([C:25]4(C#N)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:22]=[CH:23][CH:24]=3)=[CH:7][CH:8]=2)[N:3]=1.Cl[CH2:34][CH:35]=O.[O:37]1CCOCC1>O.C([O-])(O)=O.[Na+]>[C:12]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([S:18][C:19]4[CH:20]=[C:21]([C:25]5([OH:37])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)[CH:22]=[CH:23][CH:24]=4)=[CH:7][CH:8]=3)[N:3]3[CH:34]=[CH:35][N:1]=[C:2]3[CH:11]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

6

Edukt 3

HCID 33ChloroacetaldehydeHCID 312751,4-DioxaneHCID 670910914-[3-(2-Amino-4-phenyl-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Produkt 1

HCID 248757664-[3-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 516892Sodium BicarbonateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To 1t (78 mg, 0.18 mmol) in 1,4-dioxane (3 mL) and water (1 mL) was added chloroacetaldehyde (50 wt %, 0.04 mL, 0.27 mmol) and saturated aqueous NaHCO3 (2 drops), and the reaction was heated to 70° C. until no starting material was seen by tlc analysis. The mixture was concentrated and purified by preparative HPLC to give the desired product, 1u.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9cedc9dd10ab4bbcbe56d69391f3d249
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919621B2

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