Imidazole → HCID 23510773, compound

HRID 1883474Notes

Reaction equation

HRID 1883474 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:14])[CH:8]=[C:9]([N+:11]([O-])=O)[N:10]=1)=[O:5])[CH3:2].N1C=CN=C1.[F:20][C:21]([F:45])([F:44])[C:22]1[CH:27]=[CH:26][C:25]([S:28][CH2:29][CH2:30][O:31][C:32](=O)[O:33]C2C=CC([N+]([O-])=O)=CC=2)=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>CC(=O)OCC.C(Cl)Cl.CN(C1C=CN=CC=1)C.[Pd].O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:14])[CH:8]=[C:9]([NH:11][C:32]([O:31][CH2:30][CH2:29][S:28][C:25]2[CH:26]=[CH:27][C:22]([C:21]([F:20])([F:45])[F:44])=[CH:23][CH:24]=2)=[O:33])[N:10]=1)=[O:5])[CH3:2]

Participants

11

Reactant 5

HCID 795ImidazoleHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2758876Ethyl 1-methyl-4-nitroimidazole-2-carboxylateHCID 11165106HCID 11165106, compound

Product 1

HCID 23510773HCID 23510773, compoundYield 77.4%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23938PalladiumCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After 1-methyl-4-nitroimidazole-2-carboxylic acid ethyl ester (2.56 g, 12.85 mmol) was dissolved in EA (20 ml), 10% Pd/C (100 mg, catalytic weight) was added thereto. The mixture was stirred for 10 hours at room temperature under hydrogen atmosphere to reduce a nitro group (NO2) into an amino group (NH2), whereby an imidazole-type amino acid was obtained. 10% Pd/C was filtered out by celite 545 filter, and the filtrate was washed with EA and MeOH, and concentrated. To the residue were added carbonic acid 4-nitro-phenyl ester 2-(4-trifluoromethyl-phenylsulfanyl)-ethyl ester (4.52 g, 11.67 mmol) dissolved in anhydrous DCM (40 ml), DIEA (4.06 ml, 23.32 mmol), DMAP (2.85 g, 23.32 mmol), and HOBt (3.57 g, 23.32 mmol), and the mixture was stirred at room temperature. After 12 hours have passed, the reaction was stopped by adding water and the reaction mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO4 and concentrated. The residue was purified by silica gel column chromatography (EA/n-hexane=1/2, v/v) to give 1-methyl-4-[2-(4-trifluoromethyl-phenylsulfanyl)-ethoxycarbonylamino]-1H-imidazole-2-carboxylic acid ethyl ester (3.77 g, 77.40%) of a white solid.

Workup

  1. customwas obtained
  2. filtration10% Pd/C was filtered out by celite 545
  3. filtrationfilter
  4. washthe filtrate was washed with EA and MeOH
  5. concentrationconcentrated
  6. waitAfter 12 hours have passed
  7. extractionthe reaction mixture was extracted with DCM
  8. dry with materialThe organic layer was dried over anhydrous MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (EA/n-hexane=1/2

Sources & evidence

ORD record
ord-dea4481a6324450d91b547f5336a743f
Source dataset
uspto-grants-2004_07
Patent number
US06759511B2

Reaction notes

Loading…