Tetrahydrofuran → HCID 118691670, compound

HRID 927003Notes

Reaction equation

HRID 927003 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=O)[C:5]#[N:6].[C:12]([CH2:15][C:16](=O)[CH3:17])(=[O:14])C.[F:19][C:20]([F:32])([F:31])[C:21]1[CH:22]=[C:23]([NH:27][C:28]([NH2:30])=[O:29])[CH:24]=[CH:25][CH:26]=1.[O:33]1CC[CH2:35][CH2:34]1>>[CH2:34]([O:33][C:12]([C:15]1[CH:10]([C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[Br:1])[NH:30][C:28](=[O:29])[N:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:31])([F:32])[F:19])[CH:22]=2)[C:16]=1[CH3:17])=[O:14])[CH3:35]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25712(3-Trifluoromethylphenyl)ureaHCID 31261AcetylacetoneHCID 205105183-Bromo-4-formylbenzonitrile2×

Product 1

HCID 118691670HCID 118691670, compound

Procedure

3-Bromo-4-formyl-benzonitrile (intermediate 2, 3.25 g, 14.7 mmol) is stirred with acetylacetone (2.42 mL, 19.1 mmol), 3-(trifluoromethyl)phenylurea (3 g, 14.7 mmol) and polyphosphoric acid (3.02 g, 7.90 mmol) in tetrahydrofurane (80.0 mL) at 60° C. for 48 h. The reaction mixture is concentrated in vacuo and ethyl acetate and water is added and the phases are separated. The aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over MgSO4 and concentrated. Yield: 7.66 g; ESI mass spectrum: [M+H]+=508; Retention time HPLC: 1.14 min (HPLC method Z018_S04)

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo and ethyl acetate and water
  2. additionis added
  3. customthe phases are separated
  4. extractionThe aqueous phase is extracted twice with ethyl acetate
  5. washThe combined organic phases are washed with saturated sodium chloride solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custom1.14 min (HPLC method Z018_S04)

Sources & evidence

ORD record
ord-cb420192d38049d8895278f357d0a251
Source dataset
uspto-grants-2016_03
Patent number
US09290457B2

Reaction notes

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