1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-amino-1-(5-cyclopropylcarbamoyl-2-methylphenyl)-1H-pyrazole-4-carboxylic acid (2-methylcyclohexyl)-amide

HRID 884810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 884810
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([C:13](=[O:18])[NH:14][CH:15]3[CH2:17][CH2:16]3)[CH:10]=[CH:9][C:8]=2[CH3:19])[N:5]=[CH:4][C:3]=1[C:20]([OH:22])=O.[CH3:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[NH2:30].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH3:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[NH:30][C:20]([C:3]1[CH:4]=[N:5][N:6]([C:7]2[CH:12]=[C:11]([C:13](=[O:18])[NH:14][CH:15]3[CH2:17][CH2:16]3)[CH:10]=[CH:9][C:8]=2[CH3:19])[C:2]=1[NH2:1])=[O:22]

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 234322-MethylcyclohexylamineHCID 757711-HydroxybenzotriazoleHCID 580889545-amino-1-(5-cyclopropylcarbamoyl-2-methylphenyl)-1H-pyrazole-4-carboxylic acid

Produkt 1

HCID 117497965-amino-1-(5-cyclopropylcarbamoyl-2-methylphenyl)-1H-pyrazole-4-carboxylic acid (2-methylcyclohexyl)-amideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-amino-1-(5-cyclopropylcarbamoyl-2-methylphenyl)-1H-pyrazole-4-carboxylic acid (21 mg), 2-methylcyclohexylamine (10 mg), EDCI (28 mg) and HOBt (12 mg) in DMF (0.75 ml) was reacted at room temperature for 24 h. Water (4 ml) was added and the solution was extracted with ethyl acetate (3 mL×2). The organic phase was then washed with water (3 mL), dried over Na2SO4 and evaporated. The residue was purified by preparative TLC plate to give the desired product 5-amino-1-(5-cyclopropylcarbamoyl-2-methylphenyl)-1H-pyrazole-4-carboxylic acid (2-methylcyclohexyl)-amide (19 mg, 70%). HPLC (4 minute gradient) tR 2.34 min; MS m/z 396.31 [M+H]+.

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate (3 mL×2)
  2. washThe organic phase was then washed with water (3 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by preparative TLC plate

Quellen und Nachweise

ORD-Eintrag
ord-313528bec287410db1540d453eb40108
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242117B2

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