2,6-Dichloropyrazine → HCID 86686018, compound

HRID 2277723Notes

Reaction equation

HRID 2277723 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:29][C:30]1[CH:35]=[N:34][CH:33]=[C:32](Cl)[N:31]=1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([C:32]2[CH:33]=[N:34][CH:35]=[C:30]([Cl:29])[N:31]=2)[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 785042,6-DichloropyrazineHCID 3577271-Tert-butyl 3-ethyl piperidine-1,3-dicarboxylateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 86686018HCID 86686018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (90 g, 350.1 mmol) in dry THF (180 mL) at 0° C. was slowly added sodium-bis-(trimethylsilyl)-amide (1 M in THF, 450 mL, 450 mmol). The reaction mixture was stirred at the same temperature for 0.5 hr before it was slowly added to a solution of 2,6-dichloropyrazine (60 g, 401.6 mmol) in dry THF (180 mL) under argon. The resulting reaction mixture was stirred at 0° C. for 1 hr, and then allowed to warm up to room temperature, and quenched by the addition of satd. aq. solution of NH4Cl (360 mL). The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to afford a crude title product. It was then used directly in the next step without further purification.

Workup

  1. customat 0° C.
  2. customThe resulting reaction mixture
  3. stirringwas stirred at 0° C. for 1 hr
  4. customquenched by the addition of satd
  5. customThe organic layer was dried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ddd4bd223f6a4fad800e4b7571bbd2af
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

Loading…