alpha-Naphthyl isocyanate → 2-(3-(3-tert-butyl-5-(3-naphthalen-1-ylureido)-1H-pyrazol-1-yl)phenyl)acetamide

HRID 1392298

Reaktionsgleichung

Reaktionsgleichung von HRID 1392298
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:12]=[C:13]([CH2:17][C:18]([NH2:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]1([N:31]=[C:32]=[O:33])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:32]([NH:31][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)=[O:33])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18](=[O:19])[NH2:20])[CH:12]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 66589alpha-Naphthyl isocyanateHCID 218673072-(3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)acetamide

Produkt 1

HCID 218673102-(3-(3-tert-butyl-5-(3-naphthalen-1-ylureido)-1H-pyrazol-1-yl)phenyl)acetamideAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of Example N (2 g, 0.73 mmol) and 1-naphthylisocyanate (0.124 g, 0.73 mmol) in dry CH2Cl2 (4 ml) was stirred at RT under N2 for 18 h. The solvent was removed in vacuo and the crude product was washed with ethyl acetate (8 ml) and dried in vacuo to yield 1-{3-tert-butyl-1-[3-(carbamoylmethyl)phenyl)-1H-pyrazol-5-yl}-3-(naphthalene-1-yl)urea as a white solid (0.22 g). mp: 230 (dec.); 1H NMR (200 MHz, DMSO-d6): δ 9.12 (s, 1H), 8.92 (s, 1H), 8.32-8.08 (m, 3H), 7.94-7.44 (m, 8H), 6.44 (s, 1H), 3.51 (s, 2H), 1.31 (s, 9H); MS:

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. washthe crude product was washed with ethyl acetate (8 ml)
  3. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6e188fdea4f941178a5553e35ab5ee9f
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342037B2

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