Ethyl bromopyruvate → HCID 117728364, compound

HRID 1772749Notes

Reaction equation

HRID 1772749 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[N:12][CH:13]=2)[CH:5]=[N:4][C:3]=1[Cl:27].Br[CH2:29][C:30](=O)[C:31]([O:33][CH2:34][CH3:35])=[O:32]>COCCOC>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][N:14]([C:11]2[N:12]=[CH:13][C:8]([C:6]3[N:7]4[CH:29]=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:1]=[C:2]4[C:3]([Cl:27])=[N:4][CH:5]=3)=[CH:9][CH:10]=2)[CH2:15][CH2:16]1)=[O:21])([CH3:24])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 117732307tert-Butyl 4-(5-(6-amino-5-chloropyrazin-2-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 117728364HCID 117728364, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
65 °C

Procedure

Into a 50 mL sealed tube, was placed a solution of compound 90f (3.50 g, 8.53 mmol) in ethylene glycol dimethyl ether (35 mL). To the stirring mixture, ethyl 3-bromo-2-oxopropanoate (5.25 g, 26.9 mmol) was added drop-wise at 0° C. The reaction mixture was stirred overnight at 65° C. and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (3:1 v/v)) to obtain compound 90g as a yellow solid (560 mg, 13% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C23H29ClN6O4: 487.0 (M+H). found 487.1.

Workup

  1. customInto a 50 mL sealed tube
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (3:1 v/v))

Sources & evidence

ORD record
ord-c8253ca341e843038502418c96e1e315
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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