Borane;tetrahydrofuran → HCID 70979752, Verbindung

HRID 1485411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485411
B.C1COCC1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:29](=O)[C:23]3([CH2:25][CH:24]3[C:26]([O-])=[O:27])[C:18]3=[N:19][N:20]=[C:21]([CH3:22])[N:17]3[C:16]3[CH:31]=[CH:32][CH:33]=[CH:34][C:15]2=3)=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:29][C:23]3([CH2:25][CH:24]3[CH2:26][OH:27])[C:18]3=[N:19][N:20]=[C:21]([CH3:22])[N:17]3[C:16]3[CH:31]=[CH:32][CH:33]=[CH:34][C:15]2=3)=[CH:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 86718498HCID 86718498, Verbindung

Produkt 1

HCID 70979752HCID 70979752, VerbindungAusbeute 3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

BH3-THF complex (1.8 mL, 1M in THF) was added dropwise to a solution of 6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropane]-2′-carboxylate (70 mg, 0.18 mmol) in anhydrous THF (10 mL) at 0° C. The resulting mixture was stirred at room temperature for 48 hrs, then quenched with NH4Cl solution (5 mL), extracted with ethyl acetate (10 mL), dried with Na2SO4, concentrated and purified with prep-HPLC to afford (6-(4-chlorophenyl)-1-methyl-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropan]-2′-yl)methanol (2 mg, 3%) as a white solid.

Aufarbeitung

  1. customquenched with NH4Cl solution (5 mL)
  2. extractionextracted with ethyl acetate (10 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. custompurified with prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7584622419c4459db5c184de53224e0b
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422292B2

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