Carbon Tetrachloride → HCID 178433939, Verbindung

HRID 539077Notizen

Reaktionsgleichung

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:35]=[CH:34][C:26]([C:27]([NH:29][NH:30][C:31](=[NH:33])[CH3:32])=O)=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOC(C)=O.C(Cl)Cl.C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:35]=[CH:34][C:26]([C:27]5[NH:33][C:31]([CH3:32])=[N:30][N:29]=5)=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A suspension of (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-N′-(1-iminoethyl)benzohydrazide (0.049 g, 0.104 mmol) in 1:1 DCM-acetonitrile (10 mL) was treated with carbon tetrachloride (0.040 mL, 0.414 mmol), triethylamine (0.1442 mL, 1.035 mmol) and triphenylphosphine (0.1086 g, 0.414 mmol) at ambient temperature. The mixture was heated at 50° C. for 2 hours. After cooing to ambient temperature, the mixture was treated with EtOAc, washed with water, dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (2-5% MeOH in DCM) to provide (S)-4-(4-fluorophenyl)-3-(3-(4-(5-methyl-4H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.003 g, 6% yield) as a yellow oil. LCMS (APCI+) m/z 456 [M+H]+.

Aufarbeitung

customAfter cooing to ambient temperature
washwashed with water
customdried
addition(phase separator silicone treated filter paper)
concentrationconcentrated
custompurified on silica gel (2-5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag: ord-216ee27aa9d741b689b0a5cdbb59023e
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08865726B2

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