Sodium hydride → HCID 58938691, compound

HRID 598171Notes

Reaction equation

HRID 598171 reaction equation
Br[C:2]1[N:3]=[CH:4][N:5]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[CH3:31])[C:6]=1[C:7]([C:9](=[CH:15][NH:16][CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[C:10]([O:12]CC)=[O:11])=[O:8].[H-].[Na+]>CN1C(=O)CCC1>[CH3:31][C:25]1[CH:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:24]=1[N:5]1[C:6]2[C:7](=[O:8])[C:9]([C:10]([OH:12])=[O:11])=[CH:15][N:16]([CH:17]([CH2:18][CH2:19][CH3:20])[CH2:21][CH2:22][CH3:23])[C:2]=2[N:3]=[CH:4]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178443981HCID 178443981, compound

Product 1

HCID 58938691HCID 58938691, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 0.60 g (1.2 mmol) of ethyl 2-[4-bromo-1-(2,4-dimethylphenyl)-1H-imidazole-5-carbonyl]-3-(heptan-4-ylamino)acrylate in 10 mL of NMP was added 0.15 g (3.7 mmol) of sodium hydride (60% dispersion in mineral oil). The mixture was stirred at room temperature for 1 h and subsequently heated to 140° C. for 25 min. The reaction mixture was cooled to room temperature, quenched with 2 mL of saturated ammonium bicarbonate, diluted with ten volumes of water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over sodium sulfate, filtered and the resulting filtrate was concentrated to an oil. The oil was purified by flash chromatography eluting with a 3% methanol/dichloromethane mixture to give 0.12 g of the title compound as a light yellow solid. Dirty fractions were combined, concentrated and purified to give an additional 0.15 g of the title compound. The overall yield of the title compound was 0.27 g (57%).

Workup

  1. temperaturesubsequently heated to 140° C. for 25 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with 2 mL of saturated ammonium bicarbonate
  4. additiondiluted with ten volumes of water
  5. extractionextracted with ethyl acetate
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe resulting filtrate was concentrated to an oil
  10. customThe oil was purified by flash chromatography
  11. washeluting with a 3% methanol/dichloromethane mixture

Sources & evidence

ORD record
ord-d344786f289341eb98eb819aae003a78
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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