1-Methylimidazole → HCID 71279252, compound

HRID 1621109Notes

Reaction equation

HRID 1621109 reaction equation
[I-].[C:2]([O:6][C:7]([NH:9][CH2:10][CH2:11][C:12]1[N:13]([CH3:24])[CH:14]=[C:15]([C:17]2[CH:18]=[N+:19](C)[CH:20]=[CH:21][CH:22]=2)[N:16]=1)=[O:8])([CH3:5])([CH3:4])[CH3:3].CN1C=CN=C1>O>[CH3:24][N:13]1[CH:14]=[C:15]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:16]=[C:12]1[CH2:11][CH2:10][NH:9][C:7](=[O:8])[O:6][C:2]([CH3:4])([CH3:3])[CH3:5]

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 71279136HCID 71279136, compound

Product 1

HCID 71279252HCID 71279252, compoundYield 167%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-(2-(2-(tert-butoxycarbonylamino)ethyl)-1-methyl-1H-imidazol-4-yl)-1-methylpyridinium iodide (655 mg, 2.06 mmol) in 1-methylimidazole (2 mL, 25.1 mmol) was heated to 160° C. and stirred for 9 h. The reaction mixture was poured into water (5 mL) and extracted with dichloromethane (2×5 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (using silica gel amine phase and an ethyl acetate/heptane gradient) to give 1.04 g of a light yellow liquid. The residual 1-methylimidazole was distilled of in a “Kugelrohr” (ball tube) vacuum distillation apparatus at 100-120° C. at ˜0.2 mbar to yield the product as light yellow oil (102 mg, 337 μmol, 16.3%). MS: M=303.1 (M+H)+

Workup

  1. extractionextracted with dichloromethane (2×5 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography (

Sources & evidence

ORD record
ord-6570649f2a7e4f509c36c634c5105f1f
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

Loading…