2-(4-Chlorophenyl)-2-oxoethyl thiocyanate → 4-(4'-{[4-(4-Chlorophenyl)-1,3-thiazol-2-yl]amino}-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoic acid

HRID 30917

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

In a 8-mL screw-cap vial, a mixture of 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoic acid (60 mg, 0.20 mmol) and 2-(4-chlorophenyl)-2-oxoethyl thiocyanate (64 mg, 0.30 mmol) in 4 mL n-butanol was heated at 90° C. overnight. The solvent was removed under reduced pressure. The mixture was dissolved in 5 mL 1:4 MeOH/DMF and purified by reverse-phase HPLC to provide 6.8 mg (7%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 11.90 (br s, 1H), 10.50 (s, 1H), 7.75-8.00 (m, 10H), 7.50 (m, 3H), 3.30 (m, 2H), 1.05 (s, 6H); LC-MS m/z 491.2 (MH+), ret. time 3.83 min.

Aufarbeitung

customIn a 8-mL screw-cap vial
customThe solvent was removed under reduced pressure
dissolutionThe mixture was dissolved in 5 mL 1:4 MeOH/DMF
custompurified by reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag: ord-112449d16dec47329ad0d78a66e21ec8
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07423156B2

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