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

HRID 2234995노트

반응식

HRID 2234995 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-f93b0de0ecf445d395554cf2d2a4cc4c
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713978B2

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