Ammonium Chloride → 6-{[3-chloro-5-(2,2-diethoxyethoxy)pyridin-2-yl]oxy}-N-(5-methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)quinazoline-4-amine

HRID 1517297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517297
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([O:9][CH2:10][CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[CH3:24][O:25][C:26]1[N:31]=[C:30]2[S:32][C:33]([NH:35][C:36]3[C:45]4[C:40](=[CH:41][CH:42]=[C:43]([OH:46])[CH:44]=4)[N:39]=[CH:38][N:37]=3)=[N:34][C:29]2=[CH:28][CH:27]=1.[Cl-].[NH4+]>CN(C)C(=O)C>[Cl:8][C:7]1[C:2]([O:46][C:43]2[CH:44]=[C:45]3[C:40](=[CH:41][CH:42]=2)[N:39]=[CH:38][N:37]=[C:36]3[NH:35][C:33]2[S:32][C:30]3[C:29]([N:34]=2)=[CH:28][CH:27]=[C:26]([O:25][CH3:24])[N:31]=3)=[N:3][CH:4]=[C:5]([O:9][CH2:10][CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[CH:6]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 866458962,3-Dichloro-5-(2,2-diethoxyethoxy)pyridineHCID 866458994-[(5-Methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]quinazolin-6-ol

Produkt 1

HCID 866458986-{[3-chloro-5-(2,2-diethoxyethoxy)pyridin-2-yl]oxy}-N-(5-methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)quinazoline-4-amineAusbeute 2,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

2,3-Dichloro-5-(2,2-diethoxyethoxy)pyridine (240 mg, 0.85 mmol) and potassium tert-butoxide (100 mg, 0.92 mmol) were added to an N,N-dimethylacetamide suspension (1 ml) of 4-[(5-methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]quinazolin-6-ol (120 mg, 0.37 mmol), and stirred for 24 hours at 200° C. in a sealed tube. The reaction solution was cooled to room temperature, then aqueous saturated ammonium chloride solution was added, filtered, and washed with a mixed solution of chloroform/methanol (9:1). The obtained filtrate was extracted with chloroform, the organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by reversed-phase liquid chromatography (YMC CombiPrep Pro C18 AS-360-cc) to obtain 6-{[3-chloro-5-(2,2-diethoxyethoxy)pyridin-2-yl]oxy}-N-(5-methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)quinazoline-4-amine (5 mg, yield: 2%) as a pale yellow solid.

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationfiltered
  3. washwashed with a mixed solution of chloroform/methanol (9:1)
  4. extractionThe obtained filtrate was extracted with chloroform
  5. washthe organic layer was washed with water and saturated saline water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by reversed-phase liquid chromatography (YMC CombiPrep Pro C18 AS-360-cc)

Quellen und Nachweise

ORD-Eintrag
ord-3e9ab2e016524ef884846b13436e6c06
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232284B2

Notizen zur Reaktion

Wird geladen…