Propargyl bromide → 2-Ethyl-7-[(prop-2-ynyl)oxy]thiazolo[4,5-c]quinolin-4-amine

HRID 913360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913360
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:15][CH3:16])[S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:17])=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](Br)[C:25]#[CH:26]>CN(C=O)C.C1(C)C=CC=CC=1>[CH2:15]([C:13]1[S:14][C:10]2[C:9]3[CH:8]=[CH:7][C:6]([O:17][CH2:26][C:25]#[CH:24])=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:16]

Komponenten

6

Edukt 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 1363391164-Amino-2-ethylthiazolo[4,5-c]quinolin-7-ol

Produkt 1

HCID 860908572-Ethyl-7-[(prop-2-ynyl)oxy]thiazolo[4,5-c]quinolin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a stirred solution (pale orange) of 4-amino-2-ethylthiazolo[4,5-c]quinolin-7-ol (0.24 g, 1.0 mmol) was dissolved in anhydrous DMF (5 mL) was added cesium carbonate (3.0 eq., 1.0 g, 3.0 mmol) and 1.1 eq. of an 80% solution of propargyl bromide in toluene (0.16 g). The mixture was heated to 65° C. and maintained overnight. The reaction was quenched by slowly adding the reaction mixture to 10 volumes of water (50 mL). The resulting solid was collected by vacuum filtration, rinsed with acetonitrile and air dried, to provide 0.22 g of 2-ethyl-7-[(prop-2-ynyl)oxy]thiazolo[4,5-c]quinolin-4-amine as a pale-peach colored crystalline solid. MS (ACPI) m/z=284 (M+H)+.

Aufarbeitung

  1. temperaturemaintained overnight
  2. customThe reaction was quenched
  3. additionby slowly adding the reaction mixture to 10 volumes of water (50 mL)
  4. filtrationThe resulting solid was collected by vacuum filtration
  5. washrinsed with acetonitrile and air
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7052ebfac9d44cbf96dcbcfb94d8211b
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026366B2

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