1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(2-Chloro-7,7-dioxo-4,7-dihydro-1,7lambda6-dithia-4,6-diaza-inden-5-yl)-5-hydroxy-2-(3-methyl-butyl)-6-thiophen-2-yl-2H-pyridazin-3-one

HRID 30980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30980
[Cl:1][C:2]1[S:6][C:5]([S:7](=[O:10])(=[O:9])[NH2:8])=[C:4]([NH:11][C:12]([C:14]2[C:15](=[O:31])[N:16]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[N:17]=[C:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C:19]=2[OH:20])=O)[CH:3]=1.N12CCCN=C1CCCCC2>N1C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]2[S:7](=[O:10])(=[O:9])[N:8]=[C:12]([C:14]3[C:15](=[O:31])[N:16]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[N:17]=[C:18]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)[C:19]=3[OH:20])[NH:11][C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 586938565-Hydroxy-2-(3-methyl-butyl)-3-oxo-6-thiophen-2-yl-2,3-dihydro-pyridazine-4-carboxylic acid (5-chloro-2-sulfamoyl-thiophen-3-yl)-amide

Produkt 1

HCID 1361485714-(2-Chloro-7,7-dioxo-4,7-dihydro-1,7lambda6-dithia-4,6-diaza-inden-5-yl)-5-hydroxy-2-(3-methyl-butyl)-6-thiophen-2-yl-2H-pyridazin-3-oneAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of the amide intermediate (15a) (54 mg, 0.11 mmol) in anhydrous pyridine (1.5 mL) in a sealed tube, 1,8-Diazabicyclo[5,4,0] undec-7-ene (DBU) (20 μL) was added and then stirred at 140° C. (oil bath temperature) for 24 hrs. The reaction mixture was cooled to room temperature and solvent was removed in vacuo, and then the residue was further dried in high vacuum for 2 hrs. The crude material was purified by flash chromatography on silica gel using hexane and EtOAc to give the desired product (5m) (8.0 mg, 15%) as a yellow solid. LC-MS (ESI+): m/e=485.21 [M+1]+ (exact ms: 484.01); 1H NMR (400 MHz, DMSO-d6): δ 7.86 (dd, 1H, J=3.2, 1.2 Hz), 7.52 (dd, 1H, J=5.2, 0.8 Hz), 7.46 (s, 1H), 7.07 (dd, 1H, J=5.2, 3.2 Hz), 4.03 (m, 2H), 1.60 (m, 3H), 0.93 (d, 6H, J=6.4 Hz).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customsolvent was removed in vacuo
  3. customthe residue was further dried in high vacuum for 2 hrs
  4. customThe crude material was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a597ca422581475a8f70337ea01573ff
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425552B2

Notizen zur Reaktion

Wird geladen…