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

HRID 497040Notes

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-3c44365bc7f848089e18f2fbea2467f6
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949547B2

Reaction notes

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