4-Fluorophenyl isocyanate → HCID 178463336, Verbindung

HRID 1943491

Reaktionsgleichung

Reaktionsgleichung von HRID 1943491
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:28][CH2:29][CH3:30])[C:12]3[N:13]([C:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][C:22]=4[F:27])=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1.[F:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]=[O:40])=[CH:34][CH:33]=1>C1COCC1>[CH2:29]([NH:28][C:11]1[C:12]2[N:13]([C:15]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][C:22]=3[F:27])=[O:19])=[CH:16][N:17]=2)[N:14]=[C:9]([NH:8][C@H:5]2[CH2:4][CH2:3][C@H:2]([NH:1][C:39](=[O:40])[NH:38][C:35]3[CH:36]=[CH:37][C:32]([F:31])=[CH:33][CH:34]=3)[CH2:7][CH2:6]2)[CH:10]=1)[CH3:30]

Komponenten

4

Edukt 2

HCID 709554-Fluorophenyl isocyanateHCID 178463334HCID 178463334, Verbindung

Produkt 1

HCID 178463336HCID 178463336, VerbindungAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To suspension of 82B (20 mg, 0.048 mmol) in THF was added 4-fluorophenylisocyanate (6.54 μL, 0.058 mmol). The mixture was stirred at room temperature overnight. The solvent was removed under reduced and MeOH (1 mL) was added. The mixture was sonicated and the solid was collected by filtration, rinsed with a small amount of MeOH and dried under vacuum to give 8-(ethylamino)-6-((trans-4-(((4-fluorophenyl)carbamoyl)amino)cyclohexyl)amino)-N-(3-fluoro-4-pyridinyl)imidazo[1,2-b]pyridazine-3-carboxamide (20.8 mg) as an off white solid. HPLC Rt=3.176 minutes (Chromolith SpeedROD 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min gradient, monitored at 220 nm). [M+H]=550.

Aufarbeitung

  1. customThe solvent was removed
  2. additionMeOH (1 mL) was added
  3. customThe mixture was sonicated
  4. filtrationthe solid was collected by filtration
  5. washrinsed with a small amount of MeOH
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3b38bde6195d461eae3cc7aa0b958dba
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389527B2

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