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4-Methylmorpholine → HCID 178448521, Verbindung

HRID 468640
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 468640
CN1CCOCC1.[F:8][C:9]1[C:10]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C@H:35]3[CH2:40][CH2:39][C@H:38]([O:41][CH:42]4[CH2:47][CH2:46][CH2:45][CH2:44][O:43]4)[CH2:37][CH2:36]3)=[CH:29][CH:28]=2)=[CH:11][C:12](=[O:26])[N:13]([CH2:15][CH2:16][C@@:17]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:18](O)=[O:19])[CH:14]=1.ClC1N=C(OC)N=C(OC)N=1.[O:59]1[CH2:64][CH2:63][CH2:62][CH2:61][CH:60]1[O:65][NH2:66]>CC1CCCO1.O>[F:8][C:9]1[C:10]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][C@H:35]3[CH2:40][CH2:39][C@H:38]([O:41][CH:42]4[CH2:47][CH2:46][CH2:45][CH2:44][O:43]4)[CH2:37][CH2:36]3)=[CH:31][CH:32]=2)=[CH:11][C:12](=[O:26])[N:13]([CH2:15][CH2:16][C@@:17]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:18]([NH:66][O:65][CH:60]2[CH2:61][CH2:62][CH2:63][CH2:64][O:59]2)=[O:19])[CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 178448522HCID 178448522, Verbindung

Produkt 1

HCID 178448521HCID 178448521, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 73012-MethyltetrahydrofuranLösungsmittel

Versuchsvorschrift

N-Methyl morpholine (340 uL, 3.09 mmol) was added to a suspension of (2R)-4-[5-fluoro-2-oxo-4-(4-{[trans-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]methoxy}-phenyl)pyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanoic acid (1.28 g, 2.21 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (510 mg, 2.87 mmol) in 2-methyltetrahydrofuran (30 mL) and the reaction was stirred for 1 h at rt. O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine (61 mg, 0.52 mmol) was added, and the reaction was stirred overnight at rt. Water (50 mL) was added, and the mixture was extracted with EtOAc (3×150 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude material was purified via flash chromatography using an eluent of EtOAc in n-heptane (75-100%) to afford the title compound as a light brown residue (700 mg, 46%). MS (LCMS) m/z 677.4 (M+1).

Aufarbeitung

  1. stirringthe reaction was stirred overnight at rt
  2. extractionthe mixture was extracted with EtOAc (3×150 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bdfc5ed945bb43c3bb32c9789fc41c00
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08624034B2

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