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Water → 4-(3-Chloro-4 (3-fluorobenzyloxy)phenylamino)-quinazoline-6-carboxylic acid methoxy methyl amide

HRID 1801867
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1801867
CO[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)=[C:18]([Cl:31])[CH:17]=1)=[O:4].Cl.C[NH:34]OC.[Cl-].[NH4+].O.[O:40]1[CH2:44]CC[CH2:41]1>>[CH3:41][O:40][CH2:44][NH:34][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)=[C:18]([Cl:31])[CH:17]=1)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 469281154-(3-Chloro-4-(3-fluorobenzyloxy)phenylamino)-quinazoline-6-carboxylic acid methyl ester

Produkt 1

HCID 68748957
4-(3-Chloro-4 (3-fluorobenzyloxy)phenylamino)-quinazoline-6-carboxylic acid methoxy methyl amide

Versuchsvorschrift

In tetrahydrofuran (230 ml) was dissolved 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-quinazoline-6-carboxylic acid methyl ester (X-1, 11.6 g), N,O-dimethylhydroxylamine hydrochloride (7.8 g) was added, and 2 mol/L iPrMgCl tetrahydrofuran solution (79.8 ml) was added dropwise over 30 minutes under ice cooling. After completion of addition, the mixture was stirred for 20 minutes under ice cooling and, after completion of the reaction, 200 ml of aqueous saturated ammonium chloride solution was added. After 100 ml of water was added to the mixture, the mixture was extracted with ethyl acetate, and the organic layer was dried over sodium sulfate. The filtrate was concentrated to obtain 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-quinazoline-6-carboxylic acid methoxy methyl amide (XI-1, 12.7 g) as a pale yellow solid.

Aufarbeitung

  1. additionwas added
  2. additionAfter completion of addition
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-ab37c420b0b44f50a8d23767071adf7f
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08349857B2

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