Diisopropylethylamine → (S)-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)-4-iodonicotinonitrile

HRID 75917

Reaktionsgleichung

Reaktionsgleichung von HRID 75917
Cl[C:2]1[N:9]=[C:8]([NH:10][C:11]2[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[NH:13][N:12]=2)[C:7]([F:19])=[C:6]([I:20])[C:3]=1[C:4]#[N:5].[F:21][C:22]1[CH:27]=[CH:26][C:25]([C@@H:28]([NH2:30])[CH3:29])=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>CCCCO.O>[CH:16]1([C:14]2[NH:13][N:12]=[C:11]([NH:10][C:8]3[C:7]([F:19])=[C:6]([I:20])[C:3]([C:4]#[N:5])=[C:2]([NH:30][C@H:28]([C:25]4[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=4)[CH3:29])[N:9]=3)[CH:15]=2)[CH2:18][CH2:17]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 866206152-chloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-4-iodonicotinonitrile

Produkt 1

HCID 67456774(S)-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)-4-iodonicotinonitrileAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-4-iodonicotinonitrile (Method 39, 0.28 g, 0.69 mmol), (5)-1-(4-fluorophenyl)ethanamine (0.19 g, 1.3 mmol), and DIEA (0.11 g, 0.90 mmol) in n-BuOH (1 ml) was heated to 140° C. for 18 hours. The reaction was diluted with water (10 ml), extracted with DCM (2×20 ml) and the combined organic fractions were dried over Na2SO4, filtered, and then concentrated. The resulting oil was purified by column chromatography (DCM-MeOH=100:1) to give the title compound (0.07 g, 20%). MS: Calcd.: 506. Found: [M+H]+ 507.

Aufarbeitung

  1. extractionextracted with DCM (2×20 ml)
  2. dry with materialthe combined organic fractions were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting oil was purified by column chromatography (DCM-MeOH=100:1)

Quellen und Nachweise

ORD-Eintrag
ord-039937d44dde4b9c8b4dac5bbb19579d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835465B2

Verknüpfte Notizen

Wird geladen…