Water → HCID 11292979, Verbindung

HRID 1987245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987245
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:23]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[C:8]([NH:10][S:11]([C:14]2[C:19]3=[N:20][S:21][N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:9]=1)([O-])=O.O>CCOC(C)=O.C(Cl)Cl.Cl[Sn]Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:23]([N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)=[O:24])=[C:8]([NH:10][S:11]([C:14]2[C:19]3=[N:20][S:21][N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:9]=1

Komponenten

5

Edukt 2

HCID 962WaterHCID 11316813HCID 11316813, Verbindung

Produkt 1

HCID 11292979HCID 11292979, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24479Stannous ChlorideLösungsmittelHCID 21226138Dichloromethane ethylacetateLösungsmittel

Versuchsvorschrift

A solution of benzo[1,2,5]thiadiazole-4-sulfonic acid [5-nitro-2-(piperidine-1-carbonyl)-phenyl]-amide (EXAMPLE 2; 90 mg, 2.0 mmol) was dissolved in 1:1 EtOAc/DCM (10 mL), and SnCl2.2 H2O (2.3 g, 10 mmol) was added. The mixture was stirred overnight at ambient temperature then concentrated in vacuo. The resulting oil was suspended in DCM and neutralized by shaking with aqueous NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford the title compound (69 mg, 1.7 mmol, 82%). TLC (silica gel, 3:1 EtOAc/hexanes): Rf=0.42. MS (ESI): m/z 418 [M+H]+, 440 [M+Na]+. HPLC (reversed-phase): RT=8.15 min (single peak). 1H NMR (400 MHz, CDCl3): (rotameric broadening) 9.80 (s, 1H), 8.40 (m, 2H), (dd, J=8.8 Hz, 1.0 Hz, 1H), 8.15 (dd, J=7.0 Hz, 1.0 Hz, 1H), 7.82 (dd, J=8.8 Hz, 1.0 Hz, 1H), 6.77 (d, J=8.4 Hz, 1H), 6.74 (d, J=2.2 Hz, 1H), 6.19 (dd, J=8.4 Hz, 2.3 Hz, 1H), 5.75 (d, J=2.3 Hz, 2H), 2.96 (bs, 4H), 1.45 (bs, 2H), 1.24 (bs, 4H).

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. stirringneutralized by shaking with aqueous NaHCO3
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e969db8249384ff380879cc45d1d70b3
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550492B2

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