4-Methylmorpholine → HCID 58548177, Verbindung

HRID 467725

Reaktionsgleichung

Reaktionsgleichung von HRID 467725
[CH:1]([O:4][CH2:5][CH2:6][NH2:7])([CH3:3])[CH3:2].[CH:8]1([C:11]2[N:16]=[C:15]([C:17]([NH:19][C:20]3[CH:28]=[N:27][CH:26]=[CH:25][C:21]=3[C:22](O)=[O:23])=[O:18])[C:14]([NH:29][C:30]3[CH:31]=[N:32][CH:33]=[N:34][CH:35]=3)=[N:13][CH:12]=2)[CH2:10][CH2:9]1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[CH:1]([O:4][CH2:5][CH2:6][NH:7][C:22]([C:21]1[CH:25]=[CH:26][N:27]=[CH:28][C:20]=1[NH:19][C:17]([C:15]1[C:14]([NH:29][C:30]2[CH:35]=[N:34][CH:33]=[N:32][CH:31]=2)=[N:13][CH:12]=[C:11]([CH:8]2[CH2:10][CH2:9]2)[N:16]=1)=[O:18])=[O:23])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 5338662-(Propan-2-yloxy)ethan-1-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 700989283-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carbonyl]-amino}-isonicotinic acid

Produkt 1

HCID 58548177HCID 58548177, VerbindungAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred mixture of 2-aminoethyl isopropyl ether (25 mg, 242 μmol) and 3-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carbonyl]-amino}-isonicotinic acid (101 mg, 267 μmol) at rt in THF (5 ml) under an argon atmosphere were added 4-methylmorpholine (123 mg, 134 μl, 1.21 mmol) and HATU (184 mg, 485 μmol). The mixture was heated to reflux and stirring was continued for 1 day. The reaction mixture was concentrated. The crude product was purified by silica gel chromatography using an EtOAc/MeOH gradient as eluent. After trituration with MeOH, the title compound (90 mg, 80%) was obtained as yellow solid.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated
  4. customThe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b4c10af434614ecbaae0174a684336ff
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623866B2

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