2-Cyano-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzenesulfonamide → HCID 67173422, Verbindung

HRID 1256104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256104
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[S:12]([NH:15][C:16]1[CH:17]=[CH:18][C:19]2[CH2:23][O:22][B:21]([OH:24])[C:20]=2[CH:25]=1)(=[O:14])=[O:13])#[N:2]>CO.[Ni]>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([S:12]([NH:15][C:16]2[CH:17]=[CH:18][C:19]3[CH2:23][O:22][B:21]([OH:24])[C:20]=3[CH:25]=2)(=[O:13])=[O:14])=[C:3]([CH2:1][NH2:2])[CH:8]=1

Komponenten

4

Edukt 1

HCID 671740652-Cyano-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzenesulfonamide

Produkt 1

HCID 67173422HCID 67173422, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-cyano-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzenesulfonamide (3.6 g, crude, 10 mmol), NH3H2O (50 mL) and Raney Ni (3 g) in MeOH (500 mL) was stirred under 50 PSI H2 at room temperature for 20 hrs. The mixture was filtered and the filtrate was concentrated. The residue was purified by prep-HPLC (column: Luna 300×50.0 mm, 10 u; liquid phase: [A-H2O+0.025% TFA; B-MeCN] B %: 10%-45%, 25 min) to give 4-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (2.5 g, 55%) as TFA salt. 1H NMR DMSO 400 MHz δ10.05 (s, 1H), 8.16 (s, 3H), 7.47 (d, J=4.8 Hz, 1H), 7.42 (d, J=5.6 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 7.10 (q, 1H), 6.54 (s, 1H), 6.47 (q, 1H), 4.86 (s, 2H), 4.12 (d, J=5.6 Hz, 1H).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by prep-HPLC (column: Luna 300×50.0 mm, 10 u; liquid phase: [A-H2O+0.025% TFA; B-MeCN] B %: 10%-45%, 25 min)

Quellen und Nachweise

ORD-Eintrag
ord-b003b106c9584b11ae5e4012cdad6e59
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461134B2

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