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

HRID 396165Notes

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-57291b38bcaf4c02841a6b209287409d
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608063B2

Reaction notes

Loading…