Guanidine Hydrochloride → HCID 178512658, Verbindung

HRID 1067223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067223
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[H-].[Na+].Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([S:19](=[O:22])(=[O:21])[NH2:20])[CH:17]=2)[C:12]([Cl:23])=[CH:11][N:10]=1>CS(C)=O>[Cl:23][C:12]1[C:13]2[C:18](=[CH:17][C:16]([S:19](=[O:22])(=[O:21])[NH2:20])=[CH:15][CH:14]=2)[C:9]([NH:4][C:3]([NH2:5])=[NH:2])=[N:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 5742Guanidine HydrochlorideHCID 24758Sodium hydrideHCID 166586321,4-Dichloro-7-sulphamoylisoquinoline

Produkt 1

HCID 178512658HCID 178512658, VerbindungAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Guanidine hydrochloride (70 mg, 0.73 mmol) was added in one portion to a suspension of NaH (21 mg, 80% dispersion by wt in mineral oil, 0.66 mmol) in DMSO (2.0 mL) and the mixture was heated at 50° C. under N2 for 30 min. 1,4-Dichloro-7-sulphamoylisoquinoline (70 mg, 0.25 mmol) was added and the mixture heated at 90° C. for 18 h. The cooled mixture was partitioned between ethyl acetate (EtOAc) and water, and the organic phase was washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using CH2Cl2—MeOH-0.880NH3 (95:5:0.5 to 90:10:1) as eluant to give 4-chloro-1-guanidino-7-sulphamoylisoquinoline (50 mg, 0.167 mmol) as a white solid.

Aufarbeitung

  1. temperaturethe mixture heated at 90° C. for 18 h
  2. customThe cooled mixture was partitioned between ethyl acetate (EtOAc) and water
  3. washthe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography upon silica gel

Quellen und Nachweise

ORD-Eintrag
ord-52eda94d1b164f869e98c0a8b041f34f
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248738B1

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