4-Methylmorpholine → HCID 10114657, Verbindung

HRID 612021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612021
ClC(OCC(C)C)=O.CN1CCOCC1.[CH3:16][N:17]([CH3:24])[CH2:18][C:19]#[C:20][C:21](O)=[O:22].[NH2:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[N:32]=[CH:31][C:30]([C:36]#[N:37])=[C:29]2[NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([Br:45])[CH:40]=1>O1CCCC1.N1C=CC=CC=1>[Br:45][C:41]1[CH:40]=[C:39]([NH:38][C:29]2[C:28]3[C:33](=[CH:34][CH:35]=[C:26]([NH:25][C:21](=[O:22])[C:20]#[C:19][CH2:18][N:17]([CH3:24])[CH3:16])[CH:27]=3)[N:32]=[CH:31][C:30]=2[C:36]#[N:37])[CH:44]=[CH:43][CH:42]=1

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 150797524-(Dimethylamino)but-2-ynoic acid

Produkt 1

HCID 10114657HCID 10114657, VerbindungAusbeute 21,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Isobutyl chloroformate(0.260 g, 1.91 mmol) and N-methylmorpholine(0.594 g, 5.88 mmol) were added to an ice cold solution of 0.370 g (2.94 mmol) of 4-dimethylamino-2-butynoic acid in 50 mL of tetrahydrofuran under N2. After stirring for 30 min, a solution of 0.500 g (01.47 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 10 mL of pyridine was added and the mixture was stirred at 0° C. for 2 h. The reaction was quenched with ice water, and then poured into saturated sodium bicarbonate and brine. The product was collected, washed with ethyl acetate, and dried in vacuo to give 0.144 g (21%) of yellow solid; ESMS m/z 448.0 (M+H+); mp 114-118° C.

Aufarbeitung

  1. stirringthe mixture was stirred at 0° C. for 2 h
  2. customThe reaction was quenched with ice water
  3. additionpoured into saturated sodium bicarbonate and brine
  4. customThe product was collected
  5. washwashed with ethyl acetate
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-701f158aef0f4ab0afe8376c63c841d9
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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