Trifluoroacetic acid → HCID 86721453, compound

HRID 869601Notes

Reaction equation

HRID 869601 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[C:11]([CH3:12])=[N:10][CH:9]=[CH:8][N:7]3[C:13]=2[CH:14](O)[C:15]2[CH:34]=[CH:33][C:18]3/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=4[O:22][CH2:23][C:17]=3[CH:16]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[CH:1]1([C:4]2[N:5]=[C:6]3[C:11]([CH3:12])=[N:10][CH:9]=[CH:8][N:7]3[C:13]=2[CH2:14][C:15]2[CH:34]=[CH:33][C:18]3/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=4[O:22][CH2:23][C:17]=3[CH:16]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86721454HCID 86721454, compound

Product 1

HCID 86721453HCID 86721453, compoundYield 72%

Conditions

Temperature
60 °C

Procedure

[step 4] (E)-2-{8-[(2-cyclopropyl-8-methylimidazo[1,2-a]pyrazin-3-yl)(hydroxy)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (18 g, 39 mmol) obtained in step 3 was dissolved in trifluoroacetic acid (181 mL, 2.3 mol), triethylsilane (31 mL, 0.19 mol) was added, and the mixture was stirred with heating at 60° C. for 1 hr. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (100 mL) was added to the obtained residue, and the mixture was extracted 3 times with a mixed solvent of chloroform-methanol. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue was added isopropylalcohol (133 mL), and the mixture was stirred at room temperature for 4 hr and further for 1 hr under ice-cooling. The precipitated crystals were collected by suction filtration to give the title compound (13g, 72%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (100 mL)
  2. additionwas added to the obtained residue
  3. extractionthe mixture was extracted 3 times with a mixed solvent of chloroform-methanol
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the obtained residue was added isopropylalcohol (133 mL)
  7. stirringthe mixture was stirred at room temperature for 4 hr and further for 1 hr under ice-
  8. temperaturecooling
  9. filtrationThe precipitated crystals were collected by suction filtration

Sources & evidence

ORD record
ord-e49091e8857e452c9f7097aaa3e84308
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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