Ammonia → HCID 86583898, compound

HRID 1584445Notes

Reaction equation

N.C(OC([N:9]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[N:20]([N:21]([CH3:25])[C:22](=[O:24])[CH3:23])[C:19]3[CH:26]=[CH:27][CH:28]=[CH:29][C:18]=3[N:17]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.ClCCl.[IH:33]>C(OCC)C>[IH:33].[CH3:25][N:21]([N:20]1[C:19]2[CH:26]=[CH:27][CH:28]=[CH:29][C:18]=2[N:17]=[C:16]1[N:12]1[CH2:13][CH2:14][CH2:15][NH:9][CH2:10][CH2:11]1)[C:22](=[O:24])[CH3:23]

Participants

Conditions

Temperature: 40 °C

Procedure

Combine 1-(t-butoxycarbonyl)-4-1H-benzimidazol-2-yl)[1,4]diazepane (0.10 g, 0.32 mmol) and dimethylformamide (2 mL). Add sodium hydride (0.015 g, 0.62 mmol) and stir. After the gas evolution ceases, add N-methyl chloroacetamide (0.034 g, 0.32 mmol). After 12 hours, dilute the reaction mixture with water and extract with dichloromethane. Separate the layers and extract the aqueous layer with dichloromethane. Combine the organic layer and extract five times with water and then brine. Dry the organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 0.5% concentrated aqueous ammonia/1.5% methanol/dichloromethane to give 1-(t-butoxycarbonyl)-4-(1-(N-methylacetamido)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf =0.34 (silica gel, 0.5% concentrated aqueous ammonia/5% methanol/dichloromethane). Combine 1-(t-butoxycarbonyl)-4-(1-(N-methylacetamido)-1H-benzimidazol-2-yl)[1,4]diazepane (0.6 mmol) and dichloromethane (10 mL). Add aqueous 48% hydriodic acid solution (1.2 mmol). Heat to 40° C. After 6 hours, cool to ambient temperature dilute with diethyl ether (40 mL), and collect the solid to give the title compound.

Workup

temperaturecool to ambient temperature
customcollect the solid

Sources & evidence

ORD record: ord-2924d0ec7472422f8d5d6853eb26c03b
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932571

Reaction notes

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