1,2-Dichloroethane → HCID 118079349, compound

HRID 1485778Notes

Reaction equation

HRID 1485778 reaction equation
[Br:1][C:2]1[CH:18]=[N:17][C:5]2[NH:6][C@@H:7]([CH3:16])[CH2:8][N:9]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[C:4]=2[CH:3]=1.ClCCCl.C(N(CC)C(C)C)(C)C.[CH3:32][NH:33][C:34](Cl)=[O:35]>C(OCC)(=O)C>[Br:1][C:2]1[CH:18]=[N:17][C:5]2[N:6]([C:34](=[O:35])[NH:33][CH3:32])[C@@H:7]([CH3:16])[CH2:8][N:9]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 80931Methylcarbamoyl chloride2×HCID 81531Diisopropylethylamine2×HCID 118080279HCID 118080279, compound

Product 1

HCID 118079349HCID 118079349, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A reaction vial was charged with (S)-isopropyl 7-bromo-3-methyl-3,4-dihydropyrido[2,3-b]pyrazine-1(2H)-carboxylate (0.02 mmol), 1,2-dichloroethane (0.10 mL), and N,N-diisopropylethylamine (0.25 mL, 0.14 mmol). Methylcarbamic chloride (1.0 M solution in 1,2-dichloroethane, 0.120 mL, 0.120 mmol) was added, and the reaction was heated at 50° C. overnight. N,N-Diisopropylethylamine (0.25 mL, 0.14 mmol) and methylcarbamic chloride (1.0 M solution in 1,2-dichloroethane, 0.120 mL, 0.120 mmol) were added, and the reaction was heated at 80° C. overnight. The reaction was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The aqueous layer was separated and extracted with ethyl acetate and the combined organic layers were concentrated under a stream of nitrogen to afford (S)-isopropyl 7-bromo-3-methyl-4-(methylcarbamoyl)-3,4-dihydropyrido[2,3-b]pyrazine-1(2H)-carboxylate which was used in the next step without purification.

Workup

  1. customA reaction
  2. temperaturethe reaction was heated at 80° C. overnight
  3. washwashed with saturated aqueous sodium chloride solution
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate
  6. concentrationthe combined organic layers were concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-871e44bb1c1e4edeb5ce968ee8f0c2c7
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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