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

HRID 2234995ノート

反応式

HRID 2234995 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-f93b0de0ecf445d395554cf2d2a4cc4c
出典データセット
uspto-grants-2010_05
特許番号
US07713978B2

反応ノート

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