Bis-(1H-imidazol-2-YL)-methanone → HCID 86672714, compound

HRID 2369916Notes

Reaction equation

HRID 2369916 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].N1C=CN=C1[C:24](C1NC=CN=1)=[O:25]>C1COCC1>[CH3:16][O:15][CH:14]([O:17][CH3:18])[CH2:13][N:12]1[C:3]2[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][C:24]1=[O:25]

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 66889618HCID 66889618, compound

Product 1

HCID 86672714HCID 86672714, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of methyl 3-amino-2-(2,2-dimethoxyethylamino)benzoate (0.7 g, 2.4 mmol) from Step C of Example 13 in THF (23 mL) with di(1H-imidazol-2-yl)methanone (0.4 g, 2.6 mmol) was refluxed overnight. The reaction mixture was washed with saturated aqueous sodium bicarbonate, re-extracted with methylene chloride, dried (Na2SO4), filtered, and concentrated under reduced pressure to give the crude material which was purified by column chromatography (silica gel, 0% to 100% ethyl acetate in hexanes) to afford methyl 3-(2,2-dimethoxyethyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate (0.4 g, 60%): 1H NMR (300 MHz, DMSO-d6) δ 11.29 (s, 1H), 7.30 (dd, J=7.8, 1.2 Hz, 1H), 7.17 (dd, J=7.8, 1.5 Hz, 1H), 7.05 (t, J=7.8 Hz, 1H), 4.31 (t, J=5.4 Hz, 1H), 4.23-4.22 (m, 2H), 3.85 (s, 3H), 3.18 (s, 6H).

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate
  2. extractionre-extracted with methylene chloride
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude material which
  7. customwas purified by column chromatography (silica gel, 0% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-fb722f9bf9a046299e9af5929360ea07
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

Loading…