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4-Methylmorpholine → Allyl-methyl-amino-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide

HRID 1068997
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1068997
ClC(OCC(C)C)=O.CN1CCOCC1.[CH2:16]([C:19]([CH3:26])([NH2:25])[C:20]#[C:21][C:22]([OH:24])=O)[CH:17]=[CH2:18].[Br:27][C:28]1[CH:29]=[C:30]([NH:34][C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([NH2:45])[CH:43]=3)[N:38]=[CH:37][N:36]=2)[CH:31]=[CH:32][CH:33]=1>O1CCCC1.N1C=CC=CC=1>[Br:27][C:28]1[CH:29]=[C:30]([NH:34][C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([NH:45][C:22](=[O:24])[C:21]#[C:20][C:19]([CH2:16][CH:17]=[CH2:18])([CH3:26])[NH2:25])[CH:43]=3)[N:38]=[CH:37][N:36]=2)[CH:31]=[CH:32][CH:33]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamineHCID 21190742Allyl-methyl-amino-but-2-ynoic acid

Produkt 1

HCID 86757054Allyl-methyl-amino-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amideAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Isobutyl chloroformate (0.845 g, 6.2 mmol) and N-methylmorpholine (1.0 g, 9.9 mmol) were added to an ice cold solution of 1.53 g (10.0 mmol) of allyl-methyl-amino-but-2-ynoic acid in 100 mL of tetrahydrofuran under nitrogen. After stirring for 30 min, a solution of 1.500 g of N-(3-bromophenyl)-4,6-quinazolindiamine in 15 mL of pyridine was added and the mixture was stirred for 2 hr at 0° C. The reaction was then quenched with ice water, then it was poured into saturated sodium bicarbonate, and the product was extracted with ethyl acetate. Chromatography of the extract on silica gel, eluting with methanol/ethyl acetate (5:95), gave 0.750 g of allyl-methyl-amino-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide: mass spectrum (m/e): M+H 450.

Aufarbeitung

  1. stirringthe mixture was stirred for 2 hr at 0° C
  2. customThe reaction was then quenched with ice water
  3. additionit was poured into saturated sodium bicarbonate
  4. extractionthe product was extracted with ethyl acetate
  5. extractionChromatography of the extract on silica gel
  6. washeluting with methanol/ethyl acetate (5:95)

Quellen und Nachweise

ORD-Eintrag
ord-7f7128d34cc7465e8f1d7f1d7a5ad6fd
Quelldatensatz
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06251912B1

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