Potassium Carbonate → Methyl 3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}benzoate

HRID 1255835Notes

Reaction equation

[NH2:1][CH:2]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])[CH3:3].[Cl:14][C:15]1[CH:20]=[N:19][CH:18]=[C:17](Cl)[N:16]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:14][C:15]1[N:16]=[C:17]([NH:1][CH:2]([C:4]2[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=2)[C:7]([O:9][CH3:10])=[O:8])[CH3:3])[CH:18]=[N:19][CH:20]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of methyl 3-(1-aminoethyl)benzoate (120 mg, 0.67 mmol), 2,6-dichloropyrazine (150 mg, 1 mmol) and potassium carbonate (280 mg, 2 mmol) in dioxane (5 mL) was heated in a microwave reactor at 150° C. for 6 hours. After this time the mixture was cooled to room temperature, filtered and concentrated under reduced pressure to give a yellow oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give methyl 3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}benzoate (30 mg, 15%) as a pale yellow oil.

Workup

temperatureAfter this time the mixture was cooled to room temperature
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a yellow oil which
customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-38b7ad4e7d854788bb7b4d98e4c55a2c
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461161B2

Reaction notes

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