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Water → [4-(1-Cyclopropanecarbonyl-1H-pyrazol-3-yl)-phenyl]-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone

HRID 2307334
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2307334
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([C:12]([N:14]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[CH2:18][N:17]4[CH:25]=[CH:26][CH:27]=[C:16]4[CH2:15]3)=[O:13])=[CH:8][CH:7]=2)=[N:2]1.[CH:28]1([C:31](Cl)=[O:32])[CH2:30][CH2:29]1.O>N1C=CC=CC=1>[CH:28]1([C:31]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[CH:11]=[CH:10][C:9]([C:12]([N:14]4[C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=5[CH2:18][N:17]5[CH:25]=[CH:26][CH:27]=[C:16]5[CH2:15]4)=[O:13])=[CH:8][CH:7]=3)=[N:2]2)=[O:32])[CH2:30][CH2:29]1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 178519422HCID 178519422, Verbindung

Produkt 1

HCID 9932009[4-(1-Cyclopropanecarbonyl-1H-pyrazol-3-yl)-phenyl]-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanoneAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049Pyridine
Lösungsmittel

Versuchsvorschrift

To a solution of [4-(1H-pyrazol-3-yl)-phenyl]-(5H,11H-pyrrolo[2,1-c][1,4]-benzodiazepin-10-yl)-methanone (1.0 g) in dry pyridine (10 ml) was added cyclopropanecarbonyl chloride (0.44 g). After stirring at room temperature for 18 hours the reaction mixture was poured into water and the precipitate was collected by filtration. The crude product was dissolved in dichloromethane and dried over anhydrous sodium sulfate. This solution was filtered through a short column of hydrous sodium magnesium silicate, eluting with several additional volumes of dichloromethane. The eluant was concentrated on a hot plate with the gradual addition of hexane until crystallization occurred. After cooling, the crystals were collected by filtration to yield the title compound (0.88 g) was obtained as a crystalline solid, m.p. 197-199° C.

Aufarbeitung

  1. filtrationthe precipitate was collected by filtration
  2. dissolutionThe crude product was dissolved in dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThis solution was filtered through a short column of hydrous sodium magnesium silicate
  5. washeluting with several additional volumes of dichloromethane
  6. concentrationThe eluant was concentrated on a hot plate with the gradual addition of hexane until crystallization
  7. temperatureAfter cooling
  8. filtrationthe crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0378c2050a6146578f76ac1e812f8cc9
Quelldatensatz
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06831079B1

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