5-(3-(3-Morpholinopropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamide → 3-(4-Aminophenyl)-5-(3-(3-morpholinopropyl)ureido)isothiazole-4-carboxamide

HRID 870993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870993
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:30])[NH:12][C:13]2[S:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)[C:14]=2[C:27]([NH2:29])=[O:28])[CH2:3][CH2:2]1.[H][H]>CO.[Pt]=O>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:15]2[C:14]([C:27]([NH2:29])=[O:28])=[C:13]([NH:12][C:11]([NH:10][CH2:9][CH2:8][CH2:7][N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[O:30])[S:17][N:16]=2)=[CH:23][CH:22]=1

Komponenten

5

Edukt 2

HCID 716230305-(3-(3-Morpholinopropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 716213173-(4-Aminophenyl)-5-(3-(3-morpholinopropyl)ureido)isothiazole-4-carboxamideAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 5-(3-(3-morpholinopropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamide (110 mg, 0.25 mmol) and platinum oxide (25 mg, 0.11 mmol) in 15 mL MeOH was hydrogenated under 60 PSI hydrogen. After 16.5 hours, the mixture was filtered and rotary evaporated to an off-white solid. Then an additional 16 mg of impure product from another reaction was combined and this material chromatographed eluting with gradient 5% to 15% MeOH in CHCl3 to give the title compound as an off-white solid (47 mg, 40%).

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. customrotary evaporated to an off-white solid
  3. customthis material chromatographed
  4. washeluting with gradient 5% to 15% MeOH in CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-0937739898c14f4c9bcb02d9eb014ce0
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969583B2

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