alpha-Naphthyl isocyanate → 1-(3-Tert-butyl-1-(3-(2-morpholino-2-oxoethyl)phenyl)-1h-pyrazol-5-yl)-3-(naphthalen-1-yl)urea

HRID 1392297

Reaktionsgleichung

Reaktionsgleichung von HRID 1392297
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:12]=[C:13]([CH2:17][C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])[CH:14]=[CH:15][CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:26]1([N:36]=[C:37]=[O:38])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:37]([NH:36][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)=[O:38])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[O:19])[CH:12]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 66589alpha-Naphthyl isocyanateHCID 218673452-[3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl]-1-morpholinoethanone

Produkt 1

HCID 218673391-(3-Tert-butyl-1-(3-(2-morpholino-2-oxoethyl)phenyl)-1h-pyrazol-5-yl)-3-(naphthalen-1-yl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of Example L (0.2 g, 0.58 mmol) and 1-naphthylisocyanate (0.10 g, 0.6 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 purified by column chromatography using ethyl acetate/hexane/CH2Cl2 (3/1/0.7) as the eluent (0.11 g, off-white solid) to yield 1-{3-tert-butyl-1-[3-(2-morpholino-2-oxoethyl)phenyl]-1H-pyrazol-5-yl}-3-(naphthalene-1-yl)urea. mp: 194-196; 1H NMR (200 MHz, DMSO-d6): δ 9.07 (1H, s), 8.45 (s, 1H), 8.06-7.93 (m, 3H), 7.69-7.44 (m, 7H), 7.33-7.29 (d, 6.9 Hz, 1H), 6.44 (s, 1H), 3.85 (m, 2H), 3.54-3.45 (m, 8H), 1.31 (s, 9H); MS:

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-28d6bbcdf86f480f970edb121a316564
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342037B2

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