Ethyl Acetate → HCID 68582514, compound

HRID 2233943Notes

Reaction equation

HRID 2233943 reaction equation
Br[C:2]1[N:3]([CH3:10])[C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.Cl.[Cl:12][C:13]1[C:17]([Cl:18])=[C:16]([CH3:19])[NH:15][C:14]=1[C:20]([NH:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:21].CCOC(C)=O>CN1CCCC1=O>[Cl:12][C:13]1[C:17]([Cl:18])=[C:16]([CH3:19])[NH:15][C:14]=1[C:20]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([C:2]2[N:3]([CH3:10])[C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=2)[CH2:25][CH2:24]1)=[O:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 127086722-Bromo-1-methyl-5-nitro-1H-imidazoleHCID 68579996HCID 68579996, compound2×

Product 1

HCID 68582514HCID 68582514, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

TEA (0.26 ml, 1.86 mmol) was added to a mixture of 2-bromo-1-methyl-5-nitro-1H-imidazole (G. B. Barlin, J. Chem. Soc. B, 1967, 641; 126 mg, 0.61 mmol,) and 3,4-dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1), 191 mg, 0.61 mmol) in 1-methyl-2-pyrrolidinone (1.5 ml). Using a Smith Microwave Synthesizer, the mixture was subjected to single-mode microwave at 150° C. for 30 min. EtOAc was added and the solution was washed with water (2×). The organic phase was separated, dried over MgSO4, and concentrated under vacuum. The crude material was purified by chromatography on silica gel using 50% EtOAc/hexanes to give 158 mg of the title product.

Workup

  1. customat 150° C.
  2. customfor 30 min
  3. washthe solution was washed with water (2×)
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customThe crude material was purified by chromatography on silica gel using 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-1de7355ed5eb466ca99cc4ed02138f16
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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