Diisopropylethylamine → 1,1-Dimethylethyl 2-{[6-(2,4-dichlorophenyl)-5-nitropyrazin-2-yl]amino}ethylcarbamate

HRID 131123Notes

Reaction equation

HRID 131123 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[N:11][CH:12]=[C:13](Br)[N:14]=1.[C:19]([NH:26][CH2:27][CH2:28][NH2:29])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([NH:29][CH2:28][CH2:27][NH:26][C:19](=[O:20])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH:12]=[N:11][C:10]=1[N+:16]([O-:18])=[O:17]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 223185103-(2,4-Dichlorophenyl)-5-bromo-2-nitropyrazine

Product 1

HCID 120860201,1-Dimethylethyl 2-{[6-(2,4-dichlorophenyl)-5-nitropyrazin-2-yl]amino}ethylcarbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(2,4-dichlorophenyl)-5-bromo-2-nitropyrazine (1.4 g, 4.0 mmol) in DMF (10 ml) were added Boc-ethylenediamine (960 mg, 6.0 mmol) and DIPEA (1.5 ml). The solution was stirred overnight at 80° C. The solution was cooled to room temperature, taken in ethyl acetate and water. The layers were separated and the organic layer was washed with water and brine, dried, concentrated and purified to afford the title product.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-93b7d824c124478eaf32fad12f89d1b2
Source dataset
uspto-grants-2008_06
Patent number
US07384942B2

Reaction notes

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