Pyridine → Phenyl 5-cyanopyrazin-2-ylcarbamate

HRID 1827869Notes

Reaction equation

HRID 1827869 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.N1C=CC=CC=1.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18].C(OCC)(=O)C>ClCCl.C1COCC1>[C:8]([C:5]1[N:6]=[CH:7][C:2]([NH:1][C:17](=[O:18])[O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:3][CH:4]=1)#[N:9]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 139252945-Aminopyrazine-2-carbonitrile

Product 1

HCID 22064357Phenyl 5-cyanopyrazin-2-ylcarbamateYield 70.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 1B (6.0 g, 50 mmol) in a mixture of dichloromethane (100 mL) and THF (200 mL) in a room temperature water bath was treated with pyridine (4.45 mL, 55 mmol), treated dropwise with phenyl chloroformate (10.0 mL, 80 mmol), and stirred at room temperature overnight. The mixture was treated with ethyl acetate (500 mL) and filtered. The filter cake was washed with ethyl acetate and the combined filtrates were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was triturated with 30% ethyl acetate/hexanes to provide 8.50 g (70.8%) of the desired product. MS (APCI(+)) m/z 241 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 11.76 (s, 1H), 9.20 (s, 1H), 8.98 (s, 1H), 7.20–7.50 (m, 5H).

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with ethyl acetate
  3. washthe combined filtrates were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was triturated with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e3190d7164a34237b42490e81f77ca7d
Source dataset
uspto-grants-2006_06
Patent number
US07056925B2

Reaction notes

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