4-Methylmorpholine → HCID 15550658, Verbindung

HRID 276832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 276832
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[N:31][CH:32]=1)[N:29]=[CH:28][C:27]([C:33]#[N:34])=[C:26]2[NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Br:42])[CH:37]=1>O1CCCC1.N1C=CC=CC=1>[Br:42][C:38]1[CH:37]=[C:36]([NH:35][C:26]2[C:27]([C:33]#[N:34])=[CH:28][N:29]=[C:30]3[C:25]=2[CH:24]=[C:23]([NH:22][C:1](=[O:6])[C:2]#[C:3][CH3:4])[CH:32]=[N:31]3)[CH:41]=[CH:40][CH:39]=1

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 99498136-Amino-4-(3-bromo-phenylamino)-[1,8]naphthyridine-3-carbonitrile

Produkt 1

HCID 15550658HCID 15550658, VerbindungAusbeute 29,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.85 g (10.1 mmol) of tetrolic acid and 1.8 g (17.96 mmol) of N-methyl morpholine in 18 ml of tetrahydrofuran was stirred at 0° C. as 1.35 g (9.9 mmol) of isobutyl chloroformate was slowly added. After 15 min, this mixture was added to a solution of 1.3 g (3.8 mmol) of 6-amino-4-(3-bromo-phenylamino)-[1.8]naphthyridine-3-carbonitrile and 5 mg of 4-N,N-dimethylamino-pyridine in 10 ml pyridine. The mixture was stirred a room temperature for 2.25 hr. The tetrahydrofuran was removed, diluted sodium bicarbonate was added, and the solid was collected via filtration. The solid was air dried and chromatographed on silica gel eluting with ethyl acetate-methanol mixtures giving 0.46 g of the title compound as a tan powder: mass spectrum (electrospray, m/e): M+H 408.1, 406.0.

Aufarbeitung

  1. additionwas slowly added
  2. customThe tetrahydrofuran was removed
  3. additiondiluted sodium bicarbonate was added
  4. filtrationthe solid was collected via filtration
  5. customdried
  6. customchromatographed on silica gel eluting with ethyl acetate-methanol

Quellen und Nachweise

ORD-Eintrag
ord-7ef15ce723c44f52b36cff52956d54c5
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355636B1

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