Hydrochloric Acid → Ethyl 6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carboxylate

HRID 1691475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691475
I[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[N:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:6]=2[CH:34]=1.[CH:35]([Mg]Cl)([CH3:37])C.Cl.[C:41]([O-])([OH:43])=[O:42].[Na+]>C1COCC1>[F:31][C:30]([F:33])([F:32])[O:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([N:7]2[C:6]3[CH:34]=[C:2]([C:41]([O:43][CH2:35][CH3:37])=[O:42])[CH:3]=[CH:4][C:5]=3[NH:11][C:10]3[N:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:9]=3[CH2:8]2)(=[O:22])=[O:21])=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 596187318-Iodo-6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine2×HCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 59618615Ethyl 6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 8-iodo-6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (380 mg, 0.618 mmol, intermediate 61) in 2 ml of THF was added a solution of isopropyl magnesium chloride (1.54 ml, 3.08 mmol) in THF (2M) at 0° C. and the solution was stirred for 30 min at 0° C. Then the reaction mixture was added to a solution of ethyl cyanidocarbonate in 3 mL of THF and stirred for 30 min at 0° C. The reaction mixture was poured into 2 mL of 2N HCl and 5 mL of ice-water, and the pH was adjusted to 7-8 with aqueous NaHCO3 at 0° C. The solution was extracted with ethyl acetate (3×20 ml), and the combined organic extracts were dried over Na2SO4. The solution was concentrated under reduced pressure and the residue was purified by silica gel chromatography using with hexane/ethyl acetate (6/1) to give the title compound as a white solid; Mass Spectrum: m/e=562 (M+1).

Aufarbeitung

  1. stirringstirred for 30 min at 0° C
  2. extractionThe solution was extracted with ethyl acetate (3×20 ml)
  3. dry with materialthe combined organic extracts were dried over Na2SO4
  4. concentrationThe solution was concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bac094e958dd4197b2700cc17616513f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153626B2

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