1,2-Dichloro-3-isocyanatobenzene → ethyl 4-{3-t-butyl-5-[3-(2,3-dichlorophenyl)-ureido]-1H-pyrazol-1-yl}benzoate

HRID 1696428

Reaktionsgleichung

Reaktionsgleichung von HRID 1696428
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].N(C1C=CC(C(OCC)=O)=CC=1)N.C(CC#N)(=O)C(C)(C)C.[Cl:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([N:51]=[C:52]=[O:53])[C:46]=1[Cl:54]>>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:52]([NH:51][C:47]2[CH:48]=[CH:49][CH:50]=[C:45]([Cl:44])[C:46]=2[Cl:54])=[O:53])[N:7]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20][CH:21]=2)[N:6]=1)([CH3:2])([CH3:4])[CH3:3]

Komponenten

5

Edukt 4

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 792992Ethyl 4-hydrazinylbenzoateHCID 12044795ethyl 4-(3-t-butyl-5-amino-1H-pyrazol-1-yl)benzoate

Produkt 1

HCID 58851257ethyl 4-{3-t-butyl-5-[3-(2,3-dichlorophenyl)-ureido]-1H-pyrazol-1-yl}benzoateAusbeute 48 %

Versuchsvorschrift

Using General method A, ethyl 4-(3-t-butyl-5-amino-1H-pyrazol-1-yl)benzoate (1 g, 3.09 mmol, prepared from ethyl 4-hydrazinobenzoate and pivaloylacetonitrile by the procedure of Regan, et al., J. Med. Chem., 45, 2994 (2002)) and 1,2-dichloro-3-isocyanato-benzene (0.7 g, 3.71 mmol) were combined to afford ethyl 4-{3-t-butyl-5-[3-(2,3-dichlorophenyl)-ureido]-1H-pyrazol-1-yl}benzoate (0.7 g, 48% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.20 (brs, 1H), 8.77 (brs, 1H), 8.04 (m, 1H), 7.44 (brs, 4H), 7.29-7.26 (m, 2H), 6.36 (s, 1H), 4.31 (q, J=7.2 Hz, 2H), 1.27 (s, 9H), 1.26 (t, J=7.2 Hz, 3H).

Quellen und Nachweise

ORD-Eintrag
ord-6e4af1ba9def40e9a0b95c5acc9639e9
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163756B2

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