Ethyl Acetate → HCID 86588637, compound

HRID 2182161Notes

Reaction equation

HRID 2182161 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl:19][C:20]1[CH:25]=[N:24][CH:23]=[C:22](Cl)[N:21]=1.C(OCC)(=O)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)[C:22]1[CH:23]=[N:24][CH:25]=[C:20]([Cl:19])[N:21]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 63789375HCID 63789375, compound

Product 1

HCID 86588637HCID 86588637, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (3-chloro-benzyl)-carbamic acid tert-butyl ester (458 mg, 1.9 mmol) in DMF (20 mL) was treated with 60% NaH in mineral oil (152 mg, 3.79 mmol). The resulting mixture was stirred at room, temperature until the gas evolution ceased and 2,6-dichloro-pyrazine (282 mg, 1.89 mmol) was added. The reaction mixture was stirred at 80° C. until the LC/MS indicated the reaction was complete. The reaction mixture was cooled and poured into Ethyl Acetate and washed with H2O and brine. The organic layers were combined, dried (Na2SO4), and concentrated to yield the title compound I-4e (199 mg).

Workup

  1. stirringThe reaction mixture was stirred at 80° C. until the LC/MS
  2. temperatureThe reaction mixture was cooled
  3. washwashed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-555af8840f624c778529766bbe011237
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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