Diisopropylethylamine → 4-((3-ethylphenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methylamino)-3-fluorobenzonitrile

HRID 2105058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105058
CS(OS(C)(=O)=O)(=O)=O.C(C1C=C([CH:18]([C:20]2[N:21]([CH3:31])[N:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)O)C=CC=1)C.C(N([CH:38]([CH3:40])[CH3:39])CC)(C)C.[NH2:41][C:42]1[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][C:43]=1[F:50]>C(Cl)Cl>[CH2:27]([C:26]1[CH:25]=[C:23]([N:41]([CH2:18][C:20]2[N:21]([CH3:31])[N:22]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:24]=2)[C:42]2[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][C:43]=2[F:50])[CH:40]=[CH:38][CH:39]=1)[CH3:28]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 27564314-Amino-3-fluorobenzonitrileHCID 57803786(3-ethylphenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol

Produkt 1

HCID 688153324-((3-ethylphenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methylamino)-3-fluorobenzonitrileAusbeute 112,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methansulfonic anhydride (77 mg, 0.44 mmol) was added to a solution of Intermediate 370.2 (81 mg, 0.28 mmol) and diisopropylethylamine (0.2 mL, 1.16 mmol) in CH2Cl2 (2.5 mL) at 0° C. The mixture was stirred for 1 h at 0° C. and then 4-amino-3-fluorobenzonitrile (136 mg, 1 mmol) was added. The mixture was stirred for 1 h at ambient temperature, diluted with CH2Cl2 (40 mL), washed with sat. NaHCO3 and brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (EtOAc, hexanes) afforded 65 mg of Intermediate 382.1. 1H NMR (400 MHz, CDCl3) δ ppm 1.11 (t, J=7.58 Hz, 3H) 2.54 (q, J=7.58 Hz, 2H) 3.69 (s, 3 H) 5.60 (d, J=5.87 Hz, 1H) 6.10-6.16 (m, J=1.96 Hz, 1H) 7.06-7.24 (m, 6H) 7.27-7.39 (m, 3H) 7.99-8.04 (m, 2H).

Aufarbeitung

  1. stirringThe mixture was stirred for 1 h at ambient temperature
  2. washwashed with sat. NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by flash chromatography (EtOAc, hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-204e4d0995da41528539c0eb265fc126
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576098B2

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