Potassium Carbonate → HCID 59331667, compound

HRID 1255842Notes

Reaction equation

HRID 1255842 reaction equation
[NH2:1][C@H:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)[CH:7]=[N:8][CH:9]=1)[CH3:3].[Cl:20][C:21]1[CH:26]=[N:25][CH:24]=[C:23](Cl)[N:22]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:20][C:21]1[N:22]=[C:23]([NH:1][C@H:2]([C:4]2[CH:5]=[C:6]([NH:10][C:11](=[O:19])[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=3)[CH:7]=[N:8][CH:9]=2)[CH3:3])[CH:24]=[N:25][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 785042,6-DichloropyrazineHCID 59331651HCID 59331651, compound

Product 1

HCID 59331667HCID 59331667, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-{5-[(1S)-1-aminoethyl]pyridin-3-yl}-3-methylbenzamide (65 mg, 0.27 mmol), 2,6-dichloropyrazine (61 mg, 0.41 mmol) and potassium carbonate (76 mg, 0.54 mmol) in dioxane (2 mL) was heated in a microwave reactor at 150° C. for 1.5 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/methanol) to give N-(5-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}pyridin-3-yl)-3-methylbenzamide (6 mg, 6%) as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-2d0538c17f3e4b38be2a4b0545104483
Source dataset
uspto-grants-2013_06
Patent number
US08461161B2

Reaction notes

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