Ethyl bromopyruvate → HCID 117728364, compound

HRID 1772738Notes

Reaction equation

HRID 1772738 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, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 87a (1.60 g, 4.09 mmol), and ethyl 3-bromo-2-oxopropanoate (1.72 mL, 12.3 mmol) in DME (25 mL) was stirred at 80° C. under Argon for 3 days. After cooling to rt, the mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (20-60% EtOAc/heptane) to give compound 87b as a light brown solid. 1H-NMR (CDCl3; 400 MHz) δ 8.43 (d, J=2.2 Hz, 1H), 8.38 (d, J=9.0 Hz, 1H), 7.74 (dd, J=8.8, 2.4 Hz, 1H), 7.66 (d, J=2.7 Hz, 1H), 6.81 (d, J=8.8 Hz, 1H), 4.44-4.52 (m, 2H), 3.68-3.75 (m, 4H), 3.60 (d, J=5.1 Hz, 4H), 1.51 (s, 9H), 1.43 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureAfter cooling to rt
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography on silica gel (20-60% EtOAc/heptane)

Sources & evidence

ORD record
ord-7f96a160b9eb422396e4ea4d5f606ac6
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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