Water → N-[(cyclohexylamino)propyl]-4-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzamide

HRID 1875471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875471
[O:1]=[C:2]1[C:6]2[N:7]=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[NH:4][N:3]1[C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.[CH:33]1([NH:39][CH2:40][CH2:41][CH2:42][NH2:43])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.O>CC(N(C)C)=O>[CH:33]1([NH:39][CH2:40][CH2:41][CH2:42][NH:43][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:15]([N:3]3[C:2](=[O:1])[C:6]4[N:7]=[N:8][C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=5[C:5]=4[NH:4]3)=[CH:16][CH:17]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 18718N-Cyclohexyl-1,3-propanediamineHCID 81531DiisopropylethylamineHCID 589748734-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride

Produkt 1

HCID 58974890N-[(cyclohexylamino)propyl]-4-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzamideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

4-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride (97 mg, 0.30 mmol) was dissolved in anhydrous DMA (2 ml). Diisopropylethylamine (39 mg, 53 μl, 0.60 mmol) was added followed by N-cyclohexyl-1,3-propanediamine (52 mg, 0.60 mmol). The mixture was stirred for 30 min. Water (5 ml) was added to give a dark red suspension. The mixture was extracted with n-butanol (2×20 ml). The combined organic phases were washed with water and concentrated under vacuum until precipitation was observed. Hexane (20 ml) and ethyl acetate (10 ml) were added, the solids were collected by filtration and dried under vacuum. The product was isolated as a dark red powder (82 mg, 0.18 mmol, 62%). LCMS: m/z 445 [M+H]+.

Aufarbeitung

  1. customto give a dark red suspension
  2. extractionThe mixture was extracted with n-butanol (2×20 ml)
  3. washThe combined organic phases were washed with water
  4. concentrationconcentrated under vacuum until precipitation
  5. additionHexane (20 ml) and ethyl acetate (10 ml) were added
  6. filtrationthe solids were collected by filtration
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-08582a8bf0c5430d9b4d907a790ed07e
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309552B2

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