2-Amino-5-hydroxypyridine → HCID 90410647, Verbindung

HRID 626584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626584
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.CC(C)([O-])C.[K+].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH:17]=1>CC(N(C)C)=O.CCOC(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([O:8][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH:17]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 42319722-Amino-5-hydroxypyridineHCID 228320834-Chloro-N-isopropyl-pyridine-2-carboxamideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 90410647HCID 90410647, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel3×

Versuchsvorschrift

A solution of 2-amino-5-hydroxypyridine (0.446 g, 4.05 mmol) in DMA (6.75 mL) was treated with potassium tert-butoxide (0.511 g, 4.55 mmol), stirred at RT for 1 h, treated with DMA (2 mL) and a solution of 4-chloro-N-isopropylpicolinamide (0.67 g, 3.37 mmol) in DMA (6.75 mL) and stirred at RT overnight under Ar. The mixture was diluted with EtOAc, washed with 1N NaOH, then brine and the organic layer was dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (MeOH/EtOAc) to afford 4-((6-aminopyridin-3-yl)oxy)-N-isopropylpicolinamide (0.523 g, 57%). 1H NMR (400 MHz, DMSO-d6): δ 8.46 (t, J=5.6 Hz, 2H), 7.82 (d, J=2.9 Hz, 1H), 7.33 (d, J=2.6 Hz, 1H), 7.30 (dd, J=8.9, 3.0 Hz, 1H), 7.12 (dd, J=5.6, 2.6 Hz, 1H), 6.53 (d, J=8.9 Hz, 1H), 6.08 (s, 2H), 4.05-4.04 (m, 1H), 1.14 (d, J=6.6 Hz, 6H); MS (ESI) m/z: 273.1 (M+H+).

Aufarbeitung

  1. washwashed with 1N NaOH
  2. dry with materialbrine and the organic layer was dried over Na2SO4
  3. concentrationconcentrated to dryness
  4. custompurified by silica gel chromatography (MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e49da21462ff4553866797336297dbe0
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309224B2

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