Sodium Hydroxide → HCID 67416092, Verbindung

HRID 2193014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2193014
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:27]=[N:26][CH:25]=[CH:24][C:5]=1[C:6]([CH2:12][S:13]([N:16]([CH3:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])=[O:14])=[N:7]2.[OH-:28].[Na+]>C(O)(=O)C.O>[CH3:23][N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[S:13]([CH2:12][C:6]1[C:5]2[CH:24]=[CH:25][N:26]=[CH:27][C:4]=2[C:3]2[C:2](=[O:28])[NH:11][CH:10]=[CH:9][C:8]=2[N:7]=1)(=[O:14])=[O:15]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 59375562HCID 59375562, Verbindung

Produkt 1

HCID 67416092HCID 67416092, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 1-(1-chloropyrido[4,3-c]-1,6-naphthyridin-6-yl)-N-methyl-N-phenylmethanesulfonamide (45 mg, 0.113 mmol) in acetic acid (2790 μl) and water (1196 μl) was heated to 100° C. and stirred for 2 h. After cooling to room temperature, the reaction mixture was added to aqueous sodium hydroxide (1M). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford N-methyl-1-(1-oxo-1,2-dihydropyrido[4,3-c]-1,6-naphthyridin-6-yl)-N-phenylmethanesulfonamide as a yellow solid. 1H NMR (500 MHz, C2D6SO) δ 12.17 (s, 1H), 11.19 (s, 1H), 8.87 (d, 1H), 8.30 (d, 1H), 7.71 (t, 1H), 7.48 (d, 2H), 7.38 (t, 2H), 7.29 (t, 1H), 6.95 (d, 1H), 5.36 (s, 2H), 3.22 (s, 3H). LRMS (APCI) calc'd for (C14H14N3O) [M+H]+, 381.1; found 381.0.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  6. washeluting with Acetonitrile/Water+0.05% TFA

Quellen und Nachweise

ORD-Eintrag
ord-35eeaca40656457baafc6b1db5eaae63
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329722B2

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