Carbon Tetrachloride → HCID 178433979, Verbindung

HRID 421868Notizen

Reaktionsgleichung

C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.C(Cl)(Cl)(Cl)Cl.[NH:32]=[C:33]([NH:35][NH:36][C:37]([C:39]1[C:44]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([Br:52])=[CH:48][C:47]=2[F:53])=[C:43]([F:54])[C:42](=[O:55])[N:41]([CH3:56])[CH:40]=1)=O)[CH3:34]>C(Cl)Cl.C(OCC)(=O)C>[Br:52][C:49]1[CH:50]=[CH:51][C:46]([NH:45][C:44]2[C:39]([C:37]3[NH:32][C:33]([CH3:34])=[N:35][N:36]=3)=[CH:40][N:41]([CH3:56])[C:42](=[O:55])[C:43]=2[F:54])=[C:47]([F:53])[CH:48]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

PPh3 (0.12 g, 0.45 mmol), Et3N (0.17 mL, 1.21 mmol), and CCl4 (0.044 mL, 0.45 mmol) were added to a stirred suspension of 4-(4-bromo-2-fluorophenylamino)-5-fluoro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid N′-(1-imino-ethyl)-hydrazide (0.073 g, 0.18 mmol) in methylene chloride (2 mL). The reaction mixture was stirred at 50° C. for 2 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and concentrated. Purification by flash column chromatography (4% MeOH in methylene chloride) gave clean desired product (30 mg, 50%); MS APCI (−) m/z 394, 396 (M−, Br pattern) detected; 1H NMR (400 MHz, CD3OD) δ 8.16 (s, 1H), 7.31 (dd, 1H), 7.25 (d, 1H), 7.01 (td, 1H), 3.67 (s, 3H), 2.51 (s, 3H).

Aufarbeitung

temperatureAfter cooling to room temperature
washwashed with water
dry with materialdried (MgSO4)
concentrationconcentrated
customPurification by flash column chromatography (4% MeOH in methylene chloride)

Quellen und Nachweise

ORD-Eintrag: ord-1e0828ffa7b2439f98d1978a7b5a26c0
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08101611B2

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