Triethylamine → 3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)-N-(pyridin-2-yl)pyrazine-2-carboxamide
Reaction equation
[NH2:1][C:2]1[C:3]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:15])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][N:7]=1.CCN(CC)CC.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31]>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:15])=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:32]([CH2:30][CH3:31])(=[O:34])=[O:33])[CH2:12][CH2:13]2)=[CH:6][N:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-amino-6-piperazin-1-yl-N-(2-pyridyl)pyrazine-2-carboxamide (100 mg, 0.1896 mmol) was dissolved in DCM (5 mL) and treated with Et3N (57.56 mg, 79.28 μL, 0.5688 mmol) followed by ethanesulfonyl chloride (26.82 mg, 19.76 μL, 0.2086 mmol). The reaction mixture was allowed to stir for 2 hours and then diluted with dichloromethane and washed with water. The aqueous layer was extracted further with dichloromethane and the organics washed with saturated aqueous NaHCO3, dried and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography (0-5% MeOH/DCM) to afford the title compound (74.2 mg, 37% Yield). 1H NMR (400.0 MHz, DMSO) d 1.24 (t, J=7.3 Hz, 3H), 3.13 (q, J=7.4 Hz, 2H), 3.34-3.38 (m, 4H), 3.52-3.54 (m, 4H), 7.04 (s, 2H), 7.18-7.21 (m, 1H), 7.88 (s, 1H), 8.21 (d, J=8.4 Hz, 1H), 8.38 (d, J=3.2 Hz, 2H) and 10.08 (s, 1H) ppm; MS (ES+) 392.0
Workup
- washwashed with water
- extractionThe aqueous layer was extracted further with dichloromethane
- washthe organics washed with saturated aqueous NaHCO3
- customdried
- concentrationconcentrated in vacuo
- customThe residue was purified on silica gel by flash column chromatography (0-5% MeOH/DCM)
Sources & evidence
- ORD record
- ord-bb9eebcdb2a545e0ae0101c26f7de2a3
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410112B2
Reaction notes
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