Dimethylbarbituric acid → 4-(3-(5-Chloro-6-methoxypyridin-3-yl)phenylsulfonamido)pyridine-3-sulfonamide

HRID 2283342Notes

Reaction equation

C([N:4](CC=C)[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[CH:25]=[N:26][C:27]([O:31][CH3:32])=[C:28]([Cl:30])[CH:29]=2)[CH:19]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])C=C.CN1C(=O)CC(=O)N(C)C1=O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:30][C:28]1[CH:29]=[C:24]([C:20]2[CH:19]=[C:18]([S:15]([NH:14][C:13]3[CH:12]=[CH:11][N:10]=[CH:9][C:8]=3[S:5]([NH2:4])(=[O:6])=[O:7])(=[O:16])=[O:17])[CH:23]=[CH:22][CH:21]=2)[CH:25]=[N:26][C:27]=1[O:31][CH3:32]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of N,N-diallyl-4-(3-(5-chloro-6-methoxypyridin-3-yl)phenylsulfonamido)pyridine-3-sulfonamide (0.19 g, 0.36 mmol) in dichloromethane (5 mL) was added to tetrakis(triphenylphosphine)palladium(0) (0.021 g, 0.022 mmol) and 1,3-dimethylbarbituric acid (0.336 g, 2.15 mmol) under an atmosphere of argon. The reaction was heated at 100° C. for 15 min in a microwave reactor and the reaction mixture was concentrated. Purification by column chromatography, using chloroform/methanol (95:5-9:1) as the eluent, gave the title compound in 49% yield.

Workup

concentrationthe reaction mixture was concentrated
customPurification by column chromatography

Sources & evidence

ORD record: ord-a8975695a07944bfb92bdfd10d4d5882
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145380B2

Reaction notes

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