1,1'-Carbonyldiimidazole → N-cyclopropyl-4-[6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzamide

HRID 1255870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255870
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][C:10]3[N:11]([N:13]=[CH:14][C:15]=3[C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=3)[CH:12]=2)[CH:4]=[N:3]1.C1N=CN(C(N2C=NC=C2)=O)C=1.C1C=C[C:40]2N(O)N=[N:43][C:41]=2[CH:42]=1.C1(N)CC1>CN(C=O)C>[CH:41]1([NH:43][C:20](=[O:22])[C:19]2[CH:23]=[CH:24][C:16]([C:15]3[CH:14]=[N:13][N:11]4[CH:12]=[C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)[CH:8]=[N:9][C:10]=34)=[CH:17][CH:18]=2)[CH2:42][CH2:40]1

Komponenten

6

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 687753784-[6-(1-Methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzoic acid

Produkt 1

HCID 59603904N-cyclopropyl-4-[6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

4-[6-(1-Methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzoic acid (50 mg, 0.16 mmol) was dissolved in DMF (2 mL). Resin bound CDI (288 mg, 0.4 mmol), HOBT (26 mg, 0.17 mmol), and cyclopropylamine (20 mg, 0.32 mmol) was added. The reaction was sealed and heated in the microwave at 120° C. for 20 minutes. The reaction was cooled to ambient temperature, filtered and purified by reverse phase chromatography to give N-cyclopropyl-4-[6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzamide as a yellow solid: LC/MS [M+H]=359.0.

Aufarbeitung

  1. additionwas added
  2. customThe reaction was sealed
  3. temperatureThe reaction was cooled to ambient temperature
  4. filtrationfiltered
  5. custompurified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-12e3b6ad07d540a78e85673b3ad3029c
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461162B2

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