Triethylamine → HCID 86645877, Verbindung

HRID 2386794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2386794
[Cl:1][C:2]1[N:11]=[C:10](Cl)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:13][C:14]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:15]=1[CH:21]([CH3:40])[C:22]([C:28]1[CH:39]=[CH:38][C:31]2[N:32]([CH3:37])[C:33](=[O:36])[N:34]([CH3:35])[C:30]=2[CH:29]=1)([OH:27])[C:23]([F:26])([F:25])[F:24].C(N(CC)CC)C.C1N2CCN(CC2)C1>CN(C=O)C.O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([O:20][C:18]2[CH:17]=[CH:16][C:15]([CH:21]([CH3:40])[C:22]([C:28]3[CH:39]=[CH:38][C:31]4[N:32]([CH3:37])[C:33](=[O:36])[N:34]([CH3:35])[C:30]=4[CH:29]=3)([OH:27])[C:23]([F:24])([F:25])[F:26])=[C:14]([Cl:13])[CH:19]=2)=[N:11][C:2]=1[Cl:1]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 9237DabcoHCID 11106516Methyl 2,6-dichloropyridine-3-carboxylateHCID 59507321HCID 59507321, Verbindung

Produkt 1

HCID 86645877HCID 86645877, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 2,6-dichloronicotinate (CAS Reg. No. 65515-28-8, 20 mg) in DMF (0.5 ml) was added 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (Example 85, 40 mg), followed by triethyl amine (0.02 ml). The mixture was stirred for 10 min, then DABCO (2 mg) was added. The mixture was stirred at room temperature over night. Water was added to the mixture and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to an oil. The residue was purified by flash chromatography (SiO2, 1:2 EtOAc/heptane) to give the title compound (55 mg) as white foam. MS (m/e)=585.9 [M+H+].

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature over night
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe residue was purified by flash chromatography (SiO2, 1:2 EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-3855bde63221451291e92021d8e65855
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268820B2

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