Hydrogen iodide → 2-[1,4]diazepan-1-yl-1-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole dihydroiodide

HRID 2230735Notes

Reaction equation

C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:19]([CH2:20][C:21]([F:24])([F:23])[F:22])[C:18]3[CH:25]=[CH:26][CH:27]=[CH:28][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[IH:29]>CO>[IH:29].[IH:29].[N:11]1([C:15]2[N:19]([CH2:20][C:21]([F:24])([F:22])[F:23])[C:18]3[CH:25]=[CH:26][CH:27]=[CH:28][C:17]=3[N:16]=2)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

Stir a solution of 4-[1-(2,2,2-trifluoro-ethyl)-1H-benzoimidazol-2-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.43 g, 1.07 mmol), methanol (10 mL) and 57% hydroiodic acid overnight at room temperature, and then heat for two hours at 50° C. Cool, add 57% hydroiodic acid (1 mL) and heat for two hours. Concentrate in vacuo to remove the solvents, dilute the residue with methanol (150 mL), concentrate in vacuo, and triturate the residual oil with ether (300 mL) to afford a tan solid. Stir the mixture for one hour, collect the solid by vacuum filtration under nitrogen, and dry in vacuo (0.2 Torr) at 82° C. to afford 0.54 g of 2-[1,4]diazepan-1-yl-1-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole dihydroiodide, m.p. >225° C. Elemental Analysis: Calculated for C14H19F3N4.2HI: 30.35%C, 3.46%H, 10.11%N; Found 30.46%C, 3.33%H, 9.79%N.

Workup

temperatureCool
temperatureheat for two hours
concentrationConcentrate in vacuo
customto remove the solvents
additiondilute the residue with methanol (150 mL)
concentrationconcentrate in vacuo
customtriturate the residual oil with ether (300 mL)
customto afford a tan solid
customcollect the solid
filtrationby vacuum filtration under nitrogen
customdry in vacuo (0.2 Torr) at 82° C.

Sources & evidence

ORD record: ord-f02278eeb2e94c20bc2fa8f68eb7f882
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06423704B1

Reaction notes

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