4-Methylmorpholine → HCID 22466772, Verbindung

HRID 1935145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1935145
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].ClC(OCC(C)C)=O.CN1CCOCC1.[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH: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][C:39]([Br:42])=[CH:38][CH:37]=1>C1COCC1.CN(C=O)C.O>[Br:42][C:39]1[CH:40]=[CH:41][C:36]([NH:35][C:26]2[C:25]3[C:30](=[CH:31][CH:32]=[C:23]([NH:22][C:1](=[O:6])[C:2]#[C:3][CH3:4])[CH:24]=3)[N:29]=[CH:28][C:27]=2[C:33]#[N:34])=[CH:37][CH:38]=1

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 224665976-Amino-4-[(4-bromophenyl)amino]-3-quinolinecarbonitrile

Produkt 1

HCID 22466772HCID 22466772, VerbindungAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolved 310 mg (3.68 mmol) 2-butynoic acid in 20 ml THF and chilled to 0° C. under N2. Added 480 μl (3.68 mmol) isobutyl chloroformate and 410 μl (3.72 mmol) N-methylmorpholine. Stirred for 20 minutes and dropwise added a solution of 500 mg (1.47 mmol) 6-amino-4-[(4-bromophenyl)amino]-3-quinolinecarbonitrile in 1 ml DMF and 10 ml THF. Removed ice bath after 15 minutes and stirred at 25° C. overnight. Stripped solvent, slurried residue with water and collected solids. Boiled solids in ethyl acetate, collected, and dried in vacuo, giving 341 mg of yellow solid: mass spectrum (electrospray m/e): M+H=405.1, 407.1.

Aufarbeitung

  1. waitRemoved ice bath after 15 minutes
  2. stirringstirred at 25° C. overnight
  3. customcollected solids
  4. customcollected
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3e09d158e85d4b5783efe9f397e640d9
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384051B1

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