Diethyl Ether → 1-{3-[1-(1H-benzoimidazole-2-carbonyl)-azetidin-3-yl]-pyrazin-2-yl}-piperidin-4-one

HRID 1850335Notes

Reaction equation

HRID 1850335 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([C:16]2[C:21]([N:22]3[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]3)=[N:20][CH:19]=[CH:18][N:17]=2)[CH2:13]1)=[O:11].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC.CCOC(C)=O>C(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:13][CH:14]([C:16]2[C:21]([N:22]3[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]3)=[N:20][CH:19]=[CH:18][N:17]=2)[CH2:15]1)=[O:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 58547358(1H-benzoimidazol-2-yl)-{3-[3-(4-hydroxy-piperidin-1-yl)-pyrazin-2-yl]-azetidin-1-yl}-methanone

Product 1

HCID 585473681-{3-[1-(1H-benzoimidazole-2-carbonyl)-azetidin-3-yl]-pyrazin-2-yl}-piperidin-4-oneYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1H-Benzoimidazol-2-yl)-{3-[3-(4-hydroxy-piperidin-1-yl)-pyrazin-2-yl]-azetidin-1-yl}-methanone (0.16 g, 0.42 mmol) was dissolved in anhydrous CH2Cl2 (20 mL), treated with Dess-Martin Periodinane (DMP) (195 mg, 0.46 mmol, 1.1 equiv) and stirred at RT until complete conversion controlled by TLC (Petro ether:EtOAc=1:1). 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 give 1-{3-[1-(1H-benzoimidazole-2-carbonyl)-azetidin-3-yl]-pyrazin-2-yl}-piperidin-4-one (0.134 g, 0.36 mmol, 85% yield) as a white solid.

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
  5. customThe resulting residue was purified by flash chromatography (20% to 40% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-6ca89c4be05841cf9f23fe8bf104b241
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

Loading…