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Ethanol → HCID 178466889, Verbindung

HRID 450404
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 450404
[CH2:1]([O:3][C:4]1[NH:8][N:7]=[C:6]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[C:12]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=3)[CH3:21])[N:11]=2)[CH:5]=1)[CH3:2].[CH2:29](O)C.C(O)(=O)C.C(N)=N.C(OCC)(=O)C>[Cl-].[Na+].O.[Pd]>[CH2:1]([O:3][C:4]1[NH:8][N:7]=[C:6]([N:9]2[C:10]3=[N:11][C:12]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=4)[CH3:21])=[CH:13][CH:14]=[C:15]3[N:16]=[CH:29]2)[CH:5]=1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 160693Formamidine acetateHCID 178466924N2-(5-Ethoxy-1H-pyrazol-3-yl)-N6-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitropyridine-2,6-diamine2×

Produkt 1

HCID 178466889HCID 178466889, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938
Palladium
Katalysator
HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

N2-(5-Ethoxy-1H-pyrazol-3-yl)-N6-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitropyridine-2,6-diamine (Intermediate 29, 0.3 g) was dissolved into ethanol (20 mL) with Pd—C (90 mg) and a hydrogen inlet. The mixture was stirred at room temperature until no starting material was detected with TLC or LCMS. Formamidine acetate (0.5 g) was added to the filtrate after the filtration of resulting mixture. The mixture was stirred at 85° C. for 4 hours. Ethyl acetate (40 mL) was added into the resulting mixture, and brine (10 mL×3) was used to wash the organic layer. The organic layer was dried and concentrated. The resulting residue was separated by silica gel column (Ethyl acetate/MeOH) to afford 0.034 g desired product. MS (electrospray): 368 (M+1) for C18H18FN7O. 1H NMR (300 MHz, CD3OD) δ ppm 8.30 (s, 1H) 8.20 (s, 1H) 7.70 (d, 1H) 7.40 (d, 1H) 6.60 (d, 1H) 5.90 (s, 1H) 5.10 (m, 1H) 4.10 (q, 2H) 1.50 (d, 3H) 1.40 (t, 3H).

Aufarbeitung

  1. filtrationafter the filtration
  2. customof resulting mixture
  3. stirringThe mixture was stirred at 85° C. for 4 hours
  4. washto wash the organic layer
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe resulting residue was separated by silica gel column (Ethyl acetate/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-8396a3806c5441e4b2a264b8b8d6c93a
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08486966B2

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