Aminopyrazine → HCID 46866214, compound

HRID 2043471Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:11][O:10]C2=O)[CH:5]=[C:4]([C:21]2[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=2)[CH:3]=1.[NH2:27][C:28]1[CH:33]=[N:32][CH:31]=[CH:30][N:29]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+]>C(OCC)(=O)C.O1CCOCC1>[F:19][C:16]1[CH:15]=[CH:14][C:13]([CH:12]([NH:8][C:6]2[CH:5]=[C:4]([C:21]3[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=3)[CH:3]=[C:2]([NH:27][C:28]3[CH:33]=[N:32][CH:31]=[CH:30][N:29]=3)[N:7]=2)[CH2:11][OH:10])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

80 mg of 3-[6-chloro-4-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl]-4-(4-fluorophenyl)oxazolidin-2-one, 20 mg of 2-aminopyrazine, 20 mg of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 41 mg of sodium t-butoxide and 22 mg of tris(dibenzylideneacetone)(chloroform)dipalladium were added in turn to 2.5 ml of degassed 1,4-dioxane, and the mixture was stirred at 90° C. for 1 hour under argon atmosphere. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 34 mg of the objective compound as white powder.

Workup

washThe solution was washed in turn with water and brine
dry with materialdried over magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-ec3053ffec6845f28579cd368ff5ed14
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586591B2

Reaction notes

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