Methyl iodide → HCID 46185994, Verbindung

HRID 446770

Reaktionsgleichung

Reaktionsgleichung von HRID 446770
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:15][CH:14]2[C:16]([NH:18]/[N:19]=[CH:20]/[C:21]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:22]=2[CH:23]=[CH:24][N:25]=[CH:26]3)=[O:17])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:31]I>CN(C=O)C>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:15][CH:14]2[C:16]([N:18]([CH3:31])/[N:19]=[CH:20]/[C:21]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:22]=2[CH:23]=[CH:24][N:25]=[CH:26]3)=[O:17])=[CH:9][CH:8]=1)([CH3:6])([CH3:4])[CH3:5]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 445554402-(4-tert-butylphenyl)-N-[(E)-isoquinolin-5-ylmethylideneamino]cyclopropane-1-carboxamide

Produkt 1

HCID 46185994HCID 46185994, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. suspension of NaH (16 mg, 0.6 mmol) in DMF (1 mL), (E)-2-(4-tert-butylphenyl)-N′-(isoquinolin-5-ylmethylene)cyclopropanecarbohydrazide (200 mg, 0.53 mmol) was added portionwise under nitrogen atmosphere. After being stirred for 1 h at 0° C., MeI (0.15 g, 1.0 mmol) was added and the reaction mixture stirred at RT for 1 h. The reaction mixture was then quenched with ice water and stirred for an additional 10 minutes. The precipitated solid was filtered and dried in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography using 20% ethyl acetate in hexanes to afford (E)-2-(4-tert-butylphenyl)-N′-(isoquinolin-5-ylmethylene)-N-methylcyclopropanecarbohydrazide (30 mg, 50%) as an off-white solid. 1H NMR (500 MHz, CDCl3): δ 9.24 (bs, 1 H), 8.50-8.41 (m, 1 H), 8.26-8.20 (m, 1 H), 8.02-7.94 (m, 2 H), 7.66-7.58 (m, 2 H), 7.39 (d, J=7.2 Hz, 2 H), 7.14 (d, J=7.2 Hz, 2 H), 3.28 (s, 3 H), 3.39-3.12 (m, 1 H), 2.63-2.56 (m, 1 H), 1.84-1.78 (m, 1 H), 1.49-1.38 (m, 1 H), 1.37 (s, 9 H). MS: M+H: m/z=386.2 and HPLC: 91%, (Condition-G).

Aufarbeitung

  1. additionwas added portionwise under nitrogen atmosphere
  2. stirringthe reaction mixture stirred at RT for 1 h
  3. customThe reaction mixture was then quenched with ice water
  4. stirringstirred for an additional 10 minutes
  5. filtrationThe precipitated solid was filtered
  6. customdried in vacuo
  7. customto obtain the crude product
  8. customThe crude material was purified via silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e11d2896179c490c9406318bd0c42ef8
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481532B2

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