Tetrahydrofuran → 9-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one

HRID 2192962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192962
[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([NH:15][C@@H:16]([C:20]([F:23])([F:22])[F:21])[CH:17]([CH3:19])[CH3:18])=[N:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12](Cl)[N:11]=[CH:10][CH:9]=3.C1C[O:29]CC1>Cl.CCOC(C)=O>[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([NH:15][C@@H:16]([C:20]([F:23])([F:22])[F:21])[CH:17]([CH3:19])[CH3:18])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:29])[C:13]=3[C:4]=2[CH:3]=1

Komponenten

5

Edukt 2

HCID 8028TetrahydrofuranHCID 593755309-bromo-1-chloro-N-[(1R)-2-methyl-1-(trifluoromethyl)propyl]benzo[c]-1,6-naphthyridin-6-amine

Produkt 1

HCID 249053779-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

9-bromo-1-chloro-N-[(1R)-2-methyl-1-(trifluoromethyl)propyl]benzo[c]-1,6-naphthyridin-6-amine (1.0 g, 2.31 mmol) in 6 N HCl (4 mL) and THF (4 mL) was heated to 90° C. for 2 hr. The reaction was cooled and diluted with EtOAc and quenched with sat. NaHCO3. The mixture was extracted and the organic layers were separated, dried with MgSO4, filtered, and concentrated to give the crude product. Column chromatography on silica gel 100% Hex. to 100% EtOAc afforded 9-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (600 MHz, CD3OD) δ 10.1 (d, 1H), 8.31 (d, 1H), 7.75 (d, 1H), 7.40 (d, 1H), 6.65, (d, 1H), 5.46 (m, 1H), 2.35 (m, 1H), 1.12 (d, 3H), 1.06 (d, 3H). LRMS (ESI) calc'd for (C17H16BrF3N3O) [M+H]+, 414.0; found 414.0.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customquenched with sat. NaHCO3
  3. extractionThe mixture was extracted
  4. customthe organic layers were separated
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product

Quellen und Nachweise

ORD-Eintrag
ord-efe21f3b208d4767a03cff0712b273f6
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329722B2

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