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

HRID 637083Notes

Reaction equation

HRID 637083 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:19]([CH2:20][CH2:21][O:22][CH2:23][C:24]#[N:25])[C:18]3[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.ClCCl.CO.[IH:35]>C(OCC)C>[IH:35].[C:24]([CH2:23][O:22][CH2:21][CH2:20][N:19]1[C:18]2[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=2[N:16]=[C:15]1[N:11]1[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1)#[N:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 24841Hydrogen iodideHCID 18464492HCID 18464492, compound

Product 1

HCID 865838924-(1-(2-cyanomethyloxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1-(2-cyanomethyloxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane (0.36 g, 0.91 mmol), dichloromethane (15 mL), and methanol (5 mL). Cool in an ice bath and add hydriodic acid (0.25 mL, 57%, 1.86 mmol). Warm to ambient temperature. After 5 hours, concentrate the reaction mixture in vacuo to give a residue. Combine the residue and diethyl ether (40 mL) and stir. After 18 hours, decant the solvent, add diethyl ether, and stir to give a solid. Collect the solid by filtration and dry to give the title compound.

Workup

  1. temperatureCool in an ice bath
  2. concentrationconcentrate the reaction mixture in vacuo
  3. customto give a residue
  4. waitAfter 18 hours
  5. customdecant the solvent
  6. additionadd diethyl ether
  7. stirringstir
  8. customto give a solid
  9. customCollect the solid
  10. filtrationby filtration
  11. customdry

Sources & evidence

ORD record
ord-3860ad3f58714befbcbbda3082d6bc41
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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