1,3-Dichloroacetone → 4-[(4-{[(6-Amino-3,5-dicyano-4-{4-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]phenyl}pyridin-2-yl)thio]methyl}-1,3-thiazol-2-yl)amino]benzoic acid

HRID 2362809

Reaktionsgleichung

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH2:13])=[S:12])=[CH:6][CH:5]=1)([OH:3])=[O:2].Cl[CH2:15][C:16]([CH2:18]Cl)=O.[NH2:20][C:21]1[C:26]([C:27]#[N:28])=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH:37]3[CH2:41][O:40][C:39]([CH3:43])([CH3:42])[O:38]3)=[CH:31][CH:30]=2)[C:24]([C:44]#[N:45])=[C:23]([SH:46])[N:22]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:20][C:21]1[N:22]=[C:23]([S:46][CH2:18][C:16]2[N:13]=[C:11]([NH:10][C:7]3[CH:6]=[CH:5][C:4]([C:1]([OH:3])=[O:2])=[CH:9][CH:8]=3)[S:12][CH:15]=2)[C:24]([C:44]#[N:45])=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH:37]3[CH2:41][O:40][C:39]([CH3:42])([CH3:43])[O:38]3)=[CH:31][CH:30]=2)[C:26]=1[C:27]#[N:28]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

177 mg (0.90 mmol) of 4-carboxyphenylthiourea and 111 mg (0.87 mmol) of 1,3-dichloroacetone are dissolved in 3 ml of DMF, and the reaction solution is stirred at 100° C. for 60 min. After cooling, 230 mg (0.60 mmol) of the compound from Example 3A and 151 mg (1.80 mmol) of sodium bicarbonate are added, and the mixture is stirred at RT for a further 16 h. The reaction mixture is purified directly by preparative HPLC chromatography (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Aufarbeitung

temperatureAfter cooling
stirringthe mixture is stirred at RT for a further 16 h
customThe reaction mixture is purified directly by preparative HPLC chromatography (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Quellen und Nachweise

ORD-Eintrag: ord-e44f1fb762ea4f54bf275d9b7de39cfd
Quelldatensatz: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08691850B2

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