Ethyl isocyanate → 4-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamate

HRID 2117061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2117061
[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:15])[C:12]([OH:14])=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.CCN(C(C)C)C(C)C.[CH2:32]([N:34]=[C:35]=[O:36])[CH3:33]>C(Cl)Cl>[CH2:32]([NH:34][C:35](=[O:36])[O:14][C:12]1[C:11]([CH3:15])=[C:10]2[N:9]([CH:13]=1)[N:8]=[CH:7][N:6]=[C:5]2[O:4][C:3]1[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:2]=1[F:1])[CH3:33]

Komponenten

5

Edukt 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 210816464-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-ol2×

Produkt 1

HCID 210816474-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamateAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 4-(2-fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-ol (25 mg, 0.082 mmol, Compound F of Example 1), DIEA (0.017 mL, 0.1 mmol) in CH2Cl2 (5 mL) was added ethyl isocyanate (0.078 mL, 0.1 mL) and stirred at room temperature for 2 h. The reaction was quenched with water (5 mL). The organic layer was separated, dried and concentrated in vacuo. The mixture was purified by flash chromatography (1-5% Methanol/CH2Cl2) to give the title compound (12.5 mg, 32%) as a white solid.

Aufarbeitung

  1. customThe reaction was quenched with water (5 mL)
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe mixture was purified by flash chromatography (1-5% Methanol/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-04f3ec62be9f40eea4ff6568f8ac7cf1
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439246B2

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