Methyl iodide → HCID 69442168, Verbindung

HRID 1594514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594514
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.[F:21][C:22]([F:34])([F:33])[O:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=S)=[CH:26][CH:25]=1.CI.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH2:10][C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)[C:31]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([O:23][C:22]([F:21])([F:33])[F:34])=[CH:25][CH:26]=3)=[N:1][C:2]=2[CH:7]=1

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 27773384-(Trifluoromethoxy)phenyl isothiocyanateHCID 68996953Methyl 4-{[(2-amino-4-chlorophenyl)amino]methyl}benzoate

Produkt 1

HCID 69442168HCID 69442168, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

The title compound of Example 12, Step B (0.5 mmol, 145 mg) and 4-trifluoromethoxyphenyl isothiocyanate (0.5 mmol, 81 μL) were heated in DCM (1 mL) for 1 h, then allowed to stand at ambient temperature for 16 h. MeI (1.0 mmol, 62 μL), DIEA (1.0 mmol, 174 μL) and DMF (0.5 mL) were added and the solution was heated at 40° C. for 2 h. The reaction mixture was partitioned between EtOAc/brine and the organic phase was dried with Na2SO4 and concentrated in vacuo. Flash chromatography on silica eluting with 18% EtOAc in hexanes afforded the product as a beige solid. LC-MS (ESI, Method C): 3.85 min, m/z 476.1 (M+1).

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc/brine
  2. dry with materialthe organic phase was dried with Na2SO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-84f56c1863d2409fbb13a586d18fe6fa
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07301036B2

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