4-Chloro-2-(trifluoromethyl)phenyl isocyanate → 1-[3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(4-chloro-2-trifluoromethyl-phenyl)-urea

HRID 919455

Reaktionsgleichung

Reaktionsgleichung von HRID 919455
[Cl:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH2:16])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[C:20]([C:27]([F:30])([F:29])[F:28])[CH:19]=1>>[Cl:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:16][C:25]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][C:20]=2[C:27]([F:29])([F:28])[F:30])=[O:26])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Komponenten

3

Edukt 2

HCID 27332644-Chloro-2-(trifluoromethyl)phenyl isocyanateHCID 231395183-(4-Chloro-2-methyl-2H-pyrazol-3-yl)4-methoxy-phenylamine

Produkt 1

HCID 116482521-[3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(4-chloro-2-trifluoromethyl-phenyl)-ureaAusbeute 8 %

Versuchsvorschrift

3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 4-chloro-2-trifluoromethylphenyl isocyanate in a similar manner as described in Example 1.53, providing 4.4 mg (8%) of Compound 79 (Note: Compound 79 did not precipitate out. Therefore, the CH2Cl2 was removed under reduced pressure, the residue was dissolved in 5 mL DMSO, and purified by preparative HPLC): LCMS m/z (%)=461 (M+H37Cl, 60), 459 (M+H35Cl, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.99 (s, 1H), 8.30 (s, 1H), 8.16 (dd, J1=8 Hz, J2=2 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 7.66 (s, 1H), 7.64 (d, J=4 Hz, 1H), 7.45 (d, J=4 Hz, 1H), 7.43 (s, 1H), 7.12 (d, J=8 Hz, 1H), 3.79 (s, 3H), 3.63 (s, 3H).

Quellen und Nachweise

ORD-Eintrag
ord-29ed496b4a394335b067d9f2fc487c1b
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273035B2

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