1-Naphthoyl fluoride → HCID 58842868, Verbindung

HRID 491998

Reaktionsgleichung

Reaktionsgleichung von HRID 491998
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:17]([NH2:18])=[CH:16][C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14]2)[CH:8]=1)[CH3:2].[C:24]1([C:34](F)=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:17]([NH:18][C:34]([C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)=[O:35])=[CH:16][C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14]2)[CH:8]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 2632231-Naphthoyl fluorideHCID 58842892ethyl 3-(3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl)propanoate

Produkt 1

HCID 58842868HCID 58842868, VerbindungAusbeute 372,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of Example Z (315 mg, 1.0 mmol) and Barton's base (0.5 mL) in anhydrous CH2Cl2 (5 mL) under N2 was stirred at RT for 30 min, and then added to a solution of naphthalene-1-carbonyl fluoride (348 mg, 0.2 mmol) in anhydrous CH2Cl2 (5 mL). The resulting mixture was stirred at RT overnight. After quenching with water (100 mL), the reaction mixture was extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine, dried (NaSO4), filtered and concentrated under reduced pressure to yield a residue which was purified by flash chromatography to afford 3-(3-{3-t-butyl-5-[(naphthalene-1-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester, (350 mg, 74%). 1H-NMR (CDCL3): 8.29 (d, J=8.0 Hz, 1H), 7.98 (d, J=7.2 Hz, 2H), 7.89 (d, J=7.2 Hz, 1H), 7.62-7.57 (m, 3H), 7.49-7.28 (m, 4H), 7.03 (s, 1H), 3.94 (q, J=7.2 Hz, 2H), 2.96 (t, J=7.2 Hz, 2H), 2.58 (t, J=7.2 Hz, 2H), 1.45 (s, 9H), 1.13 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 470 (M+H+).

Aufarbeitung

  1. customAfter quenching with water (100 mL)
  2. extractionthe reaction mixture was extracted with ethyl acetate (3×100 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a residue which
  8. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-11924aac28104479988971c8ef9d4840
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531566B2

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