Acetonitrile → HCID 22630811, compound

HRID 2416435Notes

Reaction equation

HRID 2416435 reaction equation
FC(F)(F)C(O)=O.CO[CH:10]1[CH:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[CH2:13][CH:12](OC)O1.C(#[N:31])C>>[N:22]1[CH:23]=[CH:24][CH:25]=[N:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([C:14]2[CH:13]=[CH:12][NH:31][CH:10]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 22630777HCID 22630777, compound

Product 1

HCID 22630811HCID 22630811, compoundYield 70%

Conditions

Temperature
55 °C

Procedure

Trifluoroacetic acid (61 μL, 0.80 mmol) was added to a solution of Compound 5 (39 mg, 0.06 mmol) and 2-[4-(tetrahydro-2,5-dimethoxy-3-furanyl)phenyl]pyrimidine (24 mg, 0.08 mmol, prepared as described in Reference Example 441) in acetonitrile (1 mL) at room temperature. The reaction mixture was stirred at 55° C. for 3 h, cooled to room temperature, quenched with sat. aq. NaHCO3, extracted with dichloromethane, dried with Na2SO4, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 95:5:0.2 dichloromethane/methanol/conc. NH4OH) gave 22 mg (70%) of the title compound. MS 861 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with sat. aq. NaHCO3
  3. extractionextracted with dichloromethane
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by medium pressure liquid chromatography (SiO2, 95:5:0.2 dichloromethane/methanol/conc. NH4OH)

Sources & evidence

ORD record
ord-e2d4678c4b204a2eb505716ae508211d
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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