Acetic Anhydride → HCID 178443981, compound

HRID 598170Notes

Reaction equation

HRID 598170 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[CH3:22])[C:6]=1[C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:23](OC(=O)C)(=O)C.[NH2:30][CH:31]([CH2:35][CH2:36][CH3:37])[CH2:32][CH2:33][CH3:34]>C(OC(OCC)OCC)C>[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[CH3:22])[C:6]=1[C:7]([C:8](=[CH:23][NH:30][CH:31]([CH2:35][CH2:36][CH3:37])[CH2:32][CH2:33][CH3:34])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 386654-HeptanamineHCID 67267545HCID 67267545, compound

Product 1

HCID 178443981HCID 178443981, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
120 °C

Procedure

To 1.20 g (3.3 mmol) of ethyl 3-[4-bromo-1-(2,4-dimethylphenyl)-1H-imidazol-5-yl]-3-oxopropanoate in 1.5 mL of triethylorthoformate was added 0.68 mL (7.2 mmol) of acetic anhydride. The solution was heated to 120° C. for 90 min, cooled to room temperature and concentrated in vacuo. The crude ethoxymethylene oxobutanoate was then dissolved in 35 mL of ethanol, cooled to 0° C., treated with 0.59 mL (3.9 mmol) of 4-aminoheptane and stirred at 0° C. for 1 h. The reaction mixture was concentrated in vacuo to a thick golden oil. The crude oil was purified by flash chromatography eluting with a 25-33% ethyl acetate/hexanes gradient mixture to give 0.62 g of the title compound as a white semisolid. Dirty fractions were combined, concentrated and purified to give an additional 0.20 g of the title compound. The overall yield of the title compound was 0.82 g (36%) which was found to be 70% pure by LCMS analysis. This material was used without further purification in the next step.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude ethoxymethylene oxobutanoate was then dissolved in 35 mL of ethanol
  4. temperaturecooled to 0° C.
  5. concentrationThe reaction mixture was concentrated in vacuo to a thick golden oil
  6. customThe crude oil was purified by flash chromatography
  7. washeluting with a 25-33% ethyl acetate/hexanes gradient mixture

Sources & evidence

ORD record
ord-bab06eb8b2a145269b0e63a10161de54
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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