Binap, (A+-)- → N-[5-({2-[(6-amino-5-nitropyridin-2-yl)amino]ethyl}amino)-3-(2,4-dichlorophenyl)pyrazin-2-yl]acetamide

HRID 131122Notes

Reaction equation

C([N:4]([C:8]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[N:12][CH:11]=[C:10](Br)[N:9]=1)[C:5](=[O:7])[CH3:6])(=O)C.[NH2:23][CH2:24][CH2:25][NH:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[C:29]([NH2:36])[N:28]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:36][C:29]1[N:28]=[C:27]([NH:26][CH2:25][CH2:24][NH:23][C:11]2[N:12]=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[C:8]([NH:4][C:5](=[O:7])[CH3:6])=[N:9][CH:10]=2)[CH:32]=[CH:31][C:30]=1[N+:33]([O-:35])=[O:34]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of N-acetyl-N-[3-(2,4-dichlorophenyl)-6-bromopyrazin-2-yl]acetamide (57 mg, 0.14 mmol) in DMF (2 ml) were added (2-aminoethyl)(6-amino-5-nitro(2-pyridyl))amine (28 mg, 0.141 mmol), sodium tert-butoxide ( 20 mg, 0.21 mmol), BINAP (38 mg, 0.06 mmol) and palladium acetate (10 mg, 0.04 mmol). The reaction mixture was stirred overnight at 80° C. The solution was cooled to room temperature, taken in ethyl acetate and water. The layers were separated and the organic layer was washed with water and brine, dried, concentrated and purified to afford the title product.

Workup

temperatureThe solution was cooled to room temperature
customThe layers were separated
washthe organic layer was washed with water and brine
customdried
concentrationconcentrated
custompurified

Sources & evidence

ORD record: ord-c53ebf29b34a417180742cc162297b46
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384942B2

Reaction notes

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