Potassium Carbonate → 1-ethyl-3,3,5-trimethyl-7-{3-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-ylmethyl)benzimidazol-1-yl]propoxy}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 69055Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[CH:16]=[CH:15][C:14]2[O:17][C:18]([CH3:20])=[CH:19][C:13]=2[C:12]1=[O:21].C(=O)([O-])[O-].[K+].[K+].[CH2:28]([N:30]1[C:36](=[O:37])[C:35]([CH3:39])([CH3:38])[C:34](=[O:40])[N:33]([CH3:41])[C:32]2[CH:42]=[C:43]([O:46][CH2:47][CH2:48][CH2:49]I)[CH:44]=[CH:45][C:31]1=2)[CH3:29]>CN(C=O)C>[CH2:28]([N:30]1[C:36](=[O:37])[C:35]([CH3:38])([CH3:39])[C:34](=[O:40])[N:33]([CH3:41])[C:32]2[CH:42]=[C:43]([O:46][CH2:47][CH2:48][CH2:49][N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[C:2]3[CH2:10][N:11]3[CH:16]=[CH:15][C:14]4[O:17][C:18]([CH3:20])=[CH:19][C:13]=4[C:12]3=[O:21])[CH:44]=[CH:45][C:31]1=2)[CH3:29]

Participants

Conditions

Temperature: 60 °C

Procedure

5-(1H-Benzimidazol-2-ylmethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one (0.28 g) and potassium carbonate (0.9 g) were added to a DMF solution (2 ml) of 1-ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.43 g). The mixture was stirred at 60° C. overnight. After the reaction liquid was condensed under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→4:1). The purified product was condensed to dryness under reduced pressure to give the title compound (0.43 g) as a white amorphous solid.

Workup

customAfter the reaction liquid
customcondensed under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→4:1)
customcondensed to dryness under reduced pressure

Sources & evidence

ORD record: ord-d37c9c3d7fb3444ea76a13cd46aab495
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822453B2

Reaction notes

Loading…