4-{4-[6-Chloro-2-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-1-piperidinyl}tetrahydro-2H-pyran-4-carbonitrile → 6-Chloro-1-[1-(4-methyltetrahydro-2H-pyran-4-yl)-4-piperidinyl]-5-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

HRID 2064216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064216
[Cl:1][C:2]1[C:3]([C:26]([F:29])([F:28])[F:27])=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]4([C:23]#N)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)[C:6]=2[CH:25]=1.C[Mg]Br>O1CCCC1>[ClH:1].[Cl:1][C:2]1[C:3]([C:26]([F:27])([F:28])[F:29])=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:12][CH2:13][N:14]([C:17]4([CH3:23])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[CH2:15][CH2:16]3)[C:6]=2[CH:25]=1

Komponenten

4

Edukt 2

HCID 598501594-{4-[6-Chloro-2-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-1-piperidinyl}tetrahydro-2H-pyran-4-carbonitrileHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 691279036-Chloro-1-[1-(4-methyltetrahydro-2H-pyran-4-yl)-4-piperidinyl]-5-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-{4-[6-chloro-2-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-1-piperidinyl}tetrahydro-2H-pyran-4-carbonitrile (D65, 1160 mg, 0.37 mmol) in tetrahydrofuran (5 ml) was treated with methylmagnesium bromide (3M in diethyl ether, 1.0 ml, 3.0 mmol). After 2 h at room temperature the solution was partitioned between aqueous Rochelle salt solution and dichloromethane, and the organic layer was dried (MgSO4) and evaporated The residue was chromatographed on silica gel eluting with methanol-dichloromethane mixtures to afford the title compound, which was isolated as the hydrochloride salt triturated from diethyl ether (110 mg). MH+=418 and 420,

Aufarbeitung

  1. customAfter 2 h at room temperature the solution was partitioned between aqueous Rochelle salt solution and dichloromethane
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customevaporated The residue
  4. customwas chromatographed on silica gel eluting with methanol-dichloromethane mixtures

Quellen und Nachweise

ORD-Eintrag
ord-c2452bea3fac42b88d5063779ee0a739
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288412B2

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