Potassium Carbonate → tert-butyl 4-(1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate

HRID 706434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706434
[OH:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([CH:16]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]4)=[CH:15][C:10]=3[N:9]=[CH:8]2)=[CH:4][C:3]=1[O:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:40][C:41]1[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[N:45][CH:46]=1>CN(C)C=O.[Cl-].[NH4+]>[CH3:32][O:31][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:2]=1[O:1][CH2:40][C:41]1[CH:46]=[N:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[CH:15][C:10]=2[N:9]=[CH:8]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 137528915-(Chloromethyl)-2-methoxypyridineHCID 118114035tert-butyl 4-(1-(4-hydroxy-3-methoxybenzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate

Produkt 1

HCID 118113962tert-butyl 4-(1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl 4-(1-(4-hydroxy-3-methoxybenzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate (0.51 g, 1.16 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (0.32 g, 2.32 mmol). The mixture was treated with a solution of 5-(chloromethyl)-2-methoxypyridine (219 mg, 1.39 mmol) in N,N-dimethylformamide (2 mL) added dropwise. The mixture was stirred at room temperature. After 16 h, the mixture was diluted with saturated ammonium chloride solution (20 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (3×10 mL), dried over sodium sulfate, filtered and concentrated to afford 0.53 g (82%) of tert-butyl 4-(1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate as a light yellow solid.

Aufarbeitung

  1. additionadded dropwise
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic layers were washed with brine (3×10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ba4902c2731d46149dca8efa19dc8853
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174986B2

Notizen zur Reaktion

Wird geladen…