Triethylamine → HCID 68809854, compound

HRID 227249Notes

Reaction equation

HRID 227249 reaction equation
Cl.[NH:2]=[C:3]1[N:9]=[CH:8][CH:7]=[CH:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.C(N(CC)CC)C.Br[CH2:25][C:26]([C:28]([F:31])([F:30])[F:29])=O>O1CCOCC1>[F:29][C:28]([F:31])([F:30])[C:26]1[N:2]=[C:3]2[CH2:4][NH:5][CH2:6][CH2:7][CH2:8][N:9]2[CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 86609040HCID 86609040, compound

Product 1

HCID 68809854HCID 68809854, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of compound from Step B (0.42 g, 1.68 mmol) and triethylamine (0.64 mL, 4.6 mmol) in dioxane was added 1-bromo-3,3,3-trifluoroacetone. The resultant mixture was heated at 50° C. overnight. After solvent was removed, the residue was dissolved in isopropanol and refluxed overnight. After an aqueous work-up, the residue purified by flash chromatography (silica gel, 4% of 10% methanolic ammonium hydroxide solution in dichloromethane). The intermediate was dissolved in acidic (three drops of concentration hydrochloric acid) methoxyethanol (8 mL) and heated at 120° C. overnight. After solvent was removed, the residue was treated with 4 N hydrogen chloride in dioxane for 3 h. Purification by flash chromatography (silica gel, eluting with 6% of 10% methanolic ammonium hydroxide in dichloromethane) gave the title compound.

Workup

  1. customAfter solvent was removed
  2. dissolutionthe residue was dissolved in isopropanol
  3. temperaturerefluxed overnight
  4. customAfter an aqueous work-up, the residue purified by flash chromatography (silica gel, 4% of 10% methanolic ammonium hydroxide solution in dichloromethane)
  5. dissolutionThe intermediate was dissolved in acidic (three drops of concentration hydrochloric acid) methoxyethanol (8 mL)
  6. customAfter solvent was removed
  7. additionthe residue was treated with 4 N hydrogen chloride in dioxane for 3 h
  8. customPurification
  9. washby flash chromatography (silica gel, eluting with 6% of 10% methanolic ammonium hydroxide in dichloromethane)

Sources & evidence

ORD record
ord-fb0c6fc961f44f47b6b9d19870631ac3
Source dataset
uspto-grants-2009_07
Patent number
US07560455B2

Reaction notes

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