Sodium hydride → N, N-dicyclopentyl-4-(3H-imidazo[4,5-b]pyridin-1-ylmethyl)-3-methoxybenzamide

HRID 1708594

Reaktionsgleichung

Reaktionsgleichung von HRID 1708594
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2]1.[H-].[Na+].Br[CH2:13][C:14]1[CH:32]=[CH:31][C:17]([C:18]([N:20]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:19])=[CH:16][C:15]=1[O:33][CH3:34]>CN(C)C=O>[CH:26]1([N:20]([CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[C:18](=[O:19])[C:17]2[CH:31]=[CH:32][C:14]([CH2:13][N:1]3[C:9]4[C:4](=[N:5][CH:6]=[CH:7][CH:8]=4)[NH:3][CH2:2]3)=[C:15]([O:33][CH3:34])[CH:16]=2)[CH2:27][CH2:28][CH2:29][CH2:30]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 67504Imidazo(4,5-b)pyridineHCID 189595374-bromomethyl-3-methoxy-N,N-dicyclopentyl benzamide

Produkt 1

HCID 18959554N, N-dicyclopentyl-4-(3H-imidazo[4,5-b]pyridin-1-ylmethyl)-3-methoxybenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of imidazo[4,5-b]pyridine (350 mg, 2.94 mmol) in N,N-dimethylformamide (25 mL), sodium hydride (118 mg, 60% dispersion in mineral oil, 2.94 mmol) was added. After stirring for 2 hr, 4-bromomethyl-3-methoxy-N,N-dicyclopentyl benzamide (1.4 g, 3.57 mmol) was added in small installments over 10 min. The reaction mixture was stirred under argon at 25° C. After 18 h, the reaction was quenched by adding acetic acid (0.5 mL) and the solvent was removed under reduced pressure at <45° C. The crude mixture (2 g) was chromatographed (silica gel, CH2Cl2 -MeOH-NH4OH 90-10-1) to give the title compound. (320 mg, 26%) DSC 185° C.; Anal calcd. for C25H30N4O2 ·0.6H2O: C, 69.94; H, 7.32; N, 13.05. Found C, 69.96; H, 7.58; N, 12.68.

Aufarbeitung

  1. stirringThe reaction mixture was stirred under argon at 25° C
  2. waitAfter 18 h
  3. customthe reaction was quenched
  4. additionby adding acetic acid (0.5 mL)
  5. customthe solvent was removed under reduced pressure at <45° C
  6. customThe crude mixture (2 g) was chromatographed (silica gel, CH2Cl2 -MeOH-NH4OH 90-10-1)

Quellen und Nachweise

ORD-Eintrag
ord-8c3b35b9dc8e4e6c967f9795f4a2eeed
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05359073

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