Methyl 2-bromopropionate → HCID 19365536, compound

HRID 849957Notes

Reaction equation

HRID 849957 reaction equation
[NH2:1][C:2]1[C:3]([Cl:21])=[CH:4][C:5]([F:20])=[C:6]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=2)[CH:7]=1.Br[CH:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25]>O>[Cl:21][C:3]1[C:2]([NH:1][CH:23]([C:24]([O:26][CH3:27])=[O:25])[CH3:28])=[CH:7][C:6]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=2)=[C:5]([F:20])[CH:4]=1

Participants

4

Reactant 2

HCID 95576Methyl 2-bromopropionateHCID 19365532HCID 19365532, compound2×

Product 1

HCID 19365536HCID 19365536, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 0.12 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-23) and 247 mg of methyl 2-bromopropionate was stirred at 140° C. for 3 hours. After completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 125 mg (yield, 83%) of 3-{4-chloro-5-[1-(methoxycarbonyl)ethylamino]-2-fluorophenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-89).

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb43d275722b4744b51029d382b371ae
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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