Dimethylformamide → 1-t-butoxycarbonyl-4-(1-pentyl-1H-benzimidazol-2-yl)[1,4]diazepane

HRID 2230705Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.[H-].[Na+].[CH2:31](Br)[CH2:32][CH2:33][CH2:34][CH3:35]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Treat a solution of 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepan (0.59 g, 1.86 mmol, Preparation 9) and dimethylformamide (10 mL) with sodium hydride (0.11 g, 2.75 mmol, 60% dispersion in oil) at room temperature. After 15 minutes, add pentyl bromide (0.34 mL, 2.74 mmol, Aldrich Chemical Company) and heat overnight at 80° C. Cool the reaction and dilute with dichloromethane (150 mL). Extract the organic phase with brine, dry (Na2SO4), filter and concentrate the filtrate to afford 4-(1-pentyl-1H-benzoimidazol-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.71 g, Rf=0.87, silica gel, 95:5:0.5 dichloromethane:methanol:ammonium hydroxide).

Workup

temperatureCool
customthe reaction
extractionExtract the organic phase with brine
dry with materialdry (Na2SO4)
filtrationfilter
concentrationconcentrate the filtrate

Sources & evidence

ORD record: ord-c4b2170bb331434b84026486682d5978
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06423704B1

Reaction notes

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