Sodium Iodide → HCID 178443979, Verbindung

HRID 486086

Reaktionsgleichung

Reaktionsgleichung von HRID 486086
[SH:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[F:36])=[O:27]>CN(C)C=O.C(OCC)(=O)C>[F:36][C:30]1[CH:31]=[C:32]([F:35])[CH:33]=[CH:34][C:29]=1[NH:28][C:26](=[O:27])[N:25]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][S:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]=1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10342005N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptylureaHCID 178527819HCID 178527819, Verbindung

Produkt 1

HCID 178443979HCID 178443979, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Part B. A 100 mL flask was charged with 2-mercaptoimidazo[4,5-b]-pyridine (0.65 g, 0.0043 mol), sodium iodide (0.129 g, 0.00086 mol), and potassium carbonate (0.789 g, 0.00571 mol) in N,N-dimethylformamide (15 mL). A solution of N-(5-bromopentyl)-N-heptyl-N'-(2,4-difluorophenyl)urea (2.34 g, 0.00558 mol) in N,N-dimethylformamide (20 mL) was added and the mixture was heated to 60° C. under nitrogen atmosphere for 18 hours, then cooled and poured into ethyl acetate (100 mL). The ethyl acetate solution was washed with water (3×100 mL), dried over magnesium sulfate and concentrated. Purification by flash chromatography of the resulting residue afforded the product, which solidified upon standing overnight. The residue was recrystallized to afford the title compound (2.13 g, 0.0043 mol) as a viscous oil. 1H NMR (CDCl3) δ8.27 (dd,1H,J=5.2, 1.4 Hz), 8.06-7.98 (m,1H), 7.91 (dd,1H,J=7.9, 1.3 Hz), 7.18 (dd,1H,J=7.9, 4.9 Hz), 6.84-6.76 (m,1H), 6.49 (d,1H,J=3.3 Hz), 3.41-3.24 (m,6H), 1.94-1.84 (m,2H), 1.74-1.51 (m,6H), 1.35-1.23 (m,8H), 0.88 (t,3H,J=6.6 Hz).

Aufarbeitung

  1. temperaturecooled
  2. washThe ethyl acetate solution was washed with water (3×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification by flash chromatography of the resulting residue
  6. customafforded the product, which
  7. customThe residue was recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-7e27aa2317d24042b58255345e6a845c
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290801

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