Dicyclohexylcarbodiimide → 3-tert-butyl-N-(2-(furan-2-yl)-ethyl)-1H-pyrazole-5-carboxamide

HRID 872536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872536
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH2:8].[C:9]([C:13]1[CH:17]=[C:16]([C:18](O)=[O:19])[NH:15][N:14]=1)([CH3:12])([CH3:11])[CH3:10].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C=O)C>[C:9]([C:13]1[CH:17]=[C:16]([C:18]([NH:8][CH2:7][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:19])[NH:15][N:14]=1)([CH3:12])([CH3:10])[CH3:11]

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 11328632-(Furan-2-yl)ethan-1-amineHCID 178441096HCID 178441096, Verbindung

Produkt 1

HCID 1784410803-tert-butyl-N-(2-(furan-2-yl)-ethyl)-1H-pyrazole-5-carboxamideAusbeute 38,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(furan-2-yl)ethanamine (0.81 g, 7.30 mmol) was added to a premixed (10 min) solution of 3-tert-butyl-1H-pyrazole-5-carboxylic acid (0.61 g, 3.60 mmol), DCC (1.51 g, 7.30 mmol) and HOBt (0.99 g, 7.30 mmol) in DCM:DMF-solution (10 ml, 2:9, v/v). After stirring for 15 h at RT the reaction mixture was filtered through a pad of Celite and the filtrate was washed two times with water, evaporated to dryness and purified with CombiFlash to afford 0.36 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.27 (s, 9H), 2.84 (t, 2H), 3.46 (m, 2H), 6.17 (m, 1H), 6.35 (m, 2H), 7.52 (m, 1H), 8.08 (m, 1H), 12.89 (m, 1H).

Aufarbeitung

  1. filtrationwas filtered through a pad of Celite
  2. washthe filtrate was washed two times with water
  3. customevaporated to dryness
  4. custompurified with CombiFlash

Quellen und Nachweise

ORD-Eintrag
ord-8297af944ef9490891e27963f25f9afe
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975254B2

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