Hydrochloric Acid → HCID 89657375, Verbindung

HRID 930925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 930925
[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[C:16]2[CH:25]=[C:24](C(OCC)=O)[NH:23][C:17]=2[C:18](=[O:22])[N:19]([CH3:21])[CH:20]=1.C[Mg]Br.Cl.O1C[CH2:43][CH2:42][CH2:41]1>>[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[C:16]2[CH:25]=[C:24]([C:42]([CH3:43])=[CH2:41])[NH:23][C:17]=2[C:18](=[O:22])[N:19]([CH3:21])[CH:20]=1

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 89657495HCID 89657495, VerbindungHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 89657375HCID 89657375, VerbindungAusbeute 25 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of Example 252f (0.10 g, 0.20 mmol) in tetrahydrofuran (6 mL) stirring at 0° C. was added methylmagnesium bromide (0.498 mL, 0.498 mmol). The reaction mixture was stirred at 0° C. for 1 hour, and then aqueous HCl (1 M, 2 mL) was added. The reaction mixture was concentrated and partitioned between saturated aqueous sodium chloride (10 mL) and ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by reverse phase-HPLC (C 18 40-90% gradient acetonitrile:water (0.1% TFA)) to provide the title compound (25 mg, 25% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.05 (s, 1H), 7.98 (d, J=2.4 Hz, 1H), 7.87 (dd, J=8.7, 2.4 Hz, 1H), 7.61-7.36 (m, 3H), 7.18 (t, J=8.6 Hz, 1H), 6.98 (d, J=8.3 Hz, 1H), 6.34 (d, J=2.2 Hz, 1H), 5.85 (s, 1H), 5.07 (s, 1H), 3.60 (s, 3H), 3.26 (s, 3H), 2.02 (s, 3H). MS (ESI+) m/z 471.1 (M+1)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between saturated aqueous sodium chloride (10 mL) and ethyl acetate
  3. washThe organic phase was washed with saturated aqueous sodium chloride (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase-HPLC (C 18 40-90% gradient acetonitrile:water (0.1% TFA))

Quellen und Nachweise

ORD-Eintrag
ord-bd86653c48ec4ba5a6d515736676f9a8
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296741B2

Notizen zur Reaktion

Wird geladen…