Ethyl Acetate → HCID 58547710, compound

HRID 2207781Notes

Reaction equation

HRID 2207781 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([O:15][C:16]2[C:17]([N:22]3[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]3)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:12]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([O:15][C:16]2[C:17]([N:22]3[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]3)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 58547845HCID 58547845, compound

Product 1

HCID 58547710HCID 58547710, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)piperidin-4-ol (see EXAMPLE 1.1; 94 mg, 0.25 mmol) was dissolved in anhydrous CH2Cl2 (10 mL), treated with Dess-Martin periodinane (DMP) (195 mg, 0.50 mmol, 2.0 equiv) and stirred at room temperature until complete conversion. The organic layer was washed with an aqueous solution of NaHCO3/Na2S2O3 (3×10 mL)), dried over Na2SO4, filtered and evaporated. The resulting residue was purified by flash chromatography (20% to 40% EtOAc in petroleum ether) to 1-(3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)piperidin-4-one (75 mg, 0.20 mmol, 80% yield) as a white solid. ESI-MS (M+1): 376 calc. for C21H21N5O2 375.

Workup

  1. washThe organic layer was washed with an aqueous solution of NaHCO3/Na2S2O3 (3×10 mL)),
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-fa76472292094ba09065ee5f06fb398f
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

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