2,2-Dimethyl-4-(6-morpholino-5-nitropyridin-3-yl)morpholine → 5-(2,2-Dimethylmorpholino)-2-morpholinopyridin-3-amine

HRID 1431385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431385
[CH3:1][C:2]1([CH3:23])[O:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[N:10][C:11]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:12]([N+:14]([O-])=O)[CH:13]=2)[CH2:3]1>CO.[Pd]>[CH3:1][C:2]1([CH3:23])[CH2:3][N:4]([C:8]2[CH:13]=[C:12]([NH2:14])[C:11]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[N:10][CH:9]=2)[CH2:5][CH2:6][O:7]1

Komponenten

4

Edukt 1

HCID 596311902,2-Dimethyl-4-(6-morpholino-5-nitropyridin-3-yl)morpholine

Produkt 1

HCID 596312285-(2,2-Dimethylmorpholino)-2-morpholinopyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 2,2-dimethyl-4-(6-morpholino-5-nitropyridin-3-yl)morpholine (490 mg, 1.52 mmol; described herein) in 30 mL MeOH was reduced in a Thalles H-Cube® hydrogenator using a 10% Pd/C CatCart column (20 bar, 25° C., 1 mL/min flow rate.) The reaction mixture was then concentrated, diluted with EtOAc, and extracted with 1M HCl. The aq. layer was washed with DCM and basified with 1M NaOH. The product was extracted with EtOAc, dried (magnesium sulfate), and concentrated, affording 5-(2,2-dimethylmorpholino)-2-morpholinopyridin-3-amine as a beige powder. Mass Spectrum (ESI) m/e=293.2 (M+1).

Aufarbeitung

  1. concentrationwas then concentrated
  2. additiondiluted with EtOAc
  3. extractionextracted with 1M HCl
  4. washThe aq. layer was washed with DCM and basified with 1M NaOH
  5. extractionThe product was extracted with EtOAc
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d35c25082341449ca19ac65fe62a9fb8
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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