Triethylamine → N-(2-Benzyl-5-phenyl-2H-pyrazol-3-yl)-2-[3-(2-chloro-phenyl)-ureido]-2-methyl-propionamide

HRID 2368402

Reaktionsgleichung

Reaktionsgleichung von HRID 2368402
Cl.[NH2:2][C:3]([CH3:8])([CH3:7])[C:4](Cl)=[O:5].[CH2:9]([N:16]1[C:20]([NH2:21])=[CH:19][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[Cl:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N:42]=[C:43]=[O:44]>C(Cl)Cl>[CH2:9]([N:16]1[C:20]([NH:21][C:4](=[O:5])[C:3]([NH:2][C:43]([NH:42][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[Cl:35])=[O:44])([CH3:8])[CH3:7])=[CH:19][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 76833Chlorophenyl isocyanateHCID 6847461-benzyl-3-phenyl-1H-pyrazol-5-amineHCID 214155052-Amino-2-methylpropanoyl chloride hydrochloride

Produkt 1

HCID 44612210N-(2-Benzyl-5-phenyl-2H-pyrazol-3-yl)-2-[3-(2-chloro-phenyl)-ureido]-2-methyl-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Amino-2-methyl-propionyl chloride hydrochloride (150 mg, 1.2 mmol) and 2-benzyl-5-phenyl-2H-pyrazol-3-ylamine (200 mg, 0.8 mmol) were stirred in DCM (5 mL) containing triethyl amine (100 μL, 0.8 mmol). After two hours, 2-chlorophenyl isocyanate (220 mg, 0.9 mmol) and triethyl amine (100 μL, 0.8 mmol) were added. Purification by silica gel chromatography gave the title compound. 1H NMR (400 MHz, DMSO-D6) δ 1.44 (s, 6H) 5.23 (s, 2H) 6.54 (s, 1H) 6.92 (s, 1H) 7.17 (s, 4H) 7.24 (s, 3H) 7.36 (s, 3H) 7.55 (s, 1H) 7.74 (s, 2H) 8.04 (s, 1H) 8.15 (s, 1H) 9.81 (s, 1H). m/z 488.0 (MH+).

Aufarbeitung

  1. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b33869031f744952a7fe03b62e836fb4
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703761B2

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