Methanol → 4-(1-(4,4,4-trifluorobutyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt

HRID 1584479Notes

Reaction equation

C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:19]([CH2:20][CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24])[C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CO.[IH:33]>C(OCC)C>[IH:33].[F:26][C:23]([F:24])([F:25])[CH2:22][CH2:21][CH2:20][N:19]1[C:18]2[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=2[N:16]=[C:15]1[N:11]1[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

Combine 1-t-butoxycarbonyl-4-(1-(4,4,4-trifluorobutyl)-1H-benzimidazol-2-yl)[1,4]diazepane (1.80 g, 4.22 mmol) and methanol (15 mL). Cool in an ice bath. Add aqueous hydriodic acid (3.8 g, 2.23 mL, 57%, 16.9 mmol) and warm to ambient temperature. After 30 minutes, add aqueous hydriodic acid (1.12 mL) and heat to 50° C. After 2 hours, cool to ambient temperature and evaporate to remove most of the methanol to give a residue. Combine the residue and methanol (10 mL). Add diethyl ether (200 mL) and stir to give a solid. Decant the solvent, add diethyl ether (200 mL) and stir, collect the solid by filtration to give, after drying, the title compound: mp; 206-208° C.

Workup

temperatureCool in an ice bath
waitAfter 2 hours
temperaturecool to ambient temperature
customevaporate
customto remove most of the methanol
customto give a residue
customto give a solid
customDecant the solvent
additionadd diethyl ether (200 mL)
customcollect the solid
filtrationby filtration
customto give
customafter drying

Sources & evidence

ORD record: ord-bc415e0df799461eae7f451bbb496434
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932571

Reaction notes

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