2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → N-(2-[cis-3,5-Dimethyl-1-piperazinyl]-4-pyridinyl)-4-(5-methyl-2-furanyl)benzenesulfonamide hydrochloride

HRID 2234995Notes

Reaction equation

HRID 2234995 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:19][C:20]([CH3:23])=[CH:21][CH:22]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][N:3]=1.[CH3:24][C@H:25]1[CH2:30][NH:29][CH2:28][C@@H:27]([CH3:31])[NH:26]1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[ClH:1].[CH3:24][C@H:25]1[NH:26][C@@H:27]([CH3:31])[CH2:28][N:29]([C:2]2[CH:7]=[C:6]([NH:8][S:9]([C:12]3[CH:13]=[CH:14][C:15]([C:18]4[O:19][C:20]([CH3:23])=[CH:21][CH:22]=4)=[CH:16][CH:17]=3)(=[O:10])=[O:11])[CH:5]=[CH:4][N:3]=2)[CH2:30]1

Participants

7

Reactant 4

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 23676156Sodium t-butoxideHCID 58988132HCID 58988132, compound

Product 1

HCID 68682878N-(2-[cis-3,5-Dimethyl-1-piperazinyl]-4-pyridinyl)-4-(5-methyl-2-furanyl)benzenesulfonamide hydrochloride

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-(2-chloro-4-pyridinyl)-4-(5-methyl-2-furanyl)benzenesulfonamide (D4) (250 mg, 0.74 mmol), cis-2,6-dimethylpiperazine (170 mg, 1.48 mmol), sodium tert-butoxide (140 mg, 1.48 mmol), tris(dibenzylideneacetone)dipalladium(0) (15 mg, 5 mol %), and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (30 mg, 10 mol %) in dioxan (4 ml) was microwaved at 120° C. for 1 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was evaporated and the residue purified by column chromatography eluting with 5-10% methanol in dichloromethane. The product was dissolved in methanol and converted to the hydrochloride salt by treatment with hydrogen chloride in diethyl ether to afford the title compound (E2), MS (ES+) m/e 427 [M+H]+.

Workup

  1. customwas microwaved at 120° C. for 1 h
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. customThe aqueous phase was evaporated
  4. customthe residue purified by column chromatography
  5. washeluting with 5-10% methanol in dichloromethane
  6. dissolutionThe product was dissolved in methanol

Sources & evidence

ORD record
ord-f93b0de0ecf445d395554cf2d2a4cc4c
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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