Nitrogen → 4-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxamide

HRID 1748345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748345
[CH3:1][CH:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([OH:17])=O)[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:18])[NH:4][CH2:3]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[CH3:40][C:41]1[O:45][N:44]=[C:43]([NH2:46])[CH:42]=1.C(N(CC)C(C)C)(C)C.N#N>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:1][CH:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([NH:46][C:43]4[CH:42]=[C:41]([CH3:40])[O:45][N:44]=4)=[O:17])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:18])[NH:4][CH2:3]1

Komponenten

9

Edukt 6

HCID 947NitrogenHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 661723-Amino-5-methylisoxazoleHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 587675714-Methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid

Produkt 1

HCID 672349974-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 4-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid (50 mg, 0.21 mmol) in DMF (1 mL) are added N-hydroxybenzotriazole (39 mg, 0.29 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (61 mg, 0.32 mmol). After stirring for 10 min, 5-methyl-3-aminoisoxazole (38 mg, 0.39 mmol), N,N-diisopropylethylamine (0.07 mL, 0.42 mmol) and 4-dimethylaminopyridine (2.6 mg, 0.02 mmol) are added. The reaction mixture is heated at 50° C. for 15 h and simultaneously a stream of N2 is blown over the reaction mixture to remove DMF. The residue is cooled to room temperature and EtOAc (4 mL) and water (2 mL) are added. The resulting white solid is collected by filtration to afford the title compound (32 mg, 48%). LCMS (ESMS): m/z 325.61 (M+H+).

Aufarbeitung

  1. customto remove DMF
  2. temperatureThe residue is cooled to room temperature
  3. additionEtOAc (4 mL) and water (2 mL) are added
  4. filtrationThe resulting white solid is collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-50395783363f46f5adc43210fb01452e
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150577B2

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