Bis-(1H-imidazol-2-YL)-methanone → HCID 86672714, compound
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- washThe reaction mixture was washed with saturated aqueous sodium bicarbonate
- extractionre-extracted with methylene chloride
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customto give the crude material which
- customwas purified by column chromatography (silica gel, 0% to 100% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-e81fafa492fd41a882a6d69161c8ddcc
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045501B2
Reaction notes
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