2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → N-{3-(cis-3,5-Dimethyl-1-piperazinyl)-4-[(trifluoromethyl)oxy]phenyl}-4-(2-thienyl)benzenesulfonamide

HRID 130463ノート

反応式

HRID 130463 の反応式
Br[C:2]1[CH:3]=[C:4]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[CH3:28][C@H:29]1[CH2:34][NH:33][CH2:32][C@@H:31]([CH3:35])[NH:30]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]>[CH3:28][C@H:29]1[NH:30][C@@H:31]([CH3:35])[CH2:32][N:33]([C:2]2[CH:3]=[C:4]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:5]=[CH:6][C:7]=2[O:8][C:9]([F:12])([F:11])[F:10])[CH2:34]1

参加物

7

反応物 4

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 23676156Sodium t-butoxideHCID 69198455N-{3-Bromo-4-[(trifluoromethyl)oxy]phenyl}-4-(2-thienyl)benzenesulfonamide

生成物 1

HCID 59007044N-{3-(cis-3,5-Dimethyl-1-piperazinyl)-4-[(trifluoromethyl)oxy]phenyl}-4-(2-thienyl)benzenesulfonamide

試薬・触媒・溶媒 2

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

実験手順

The product of Step 2 (162 mg, 0.34 mmol), cis-2,6-dimethyl piperazine (78 mg, 0.68 mmol), sodium tert-butoxide (169 mg, 0.68 mmol), tris(dibenzylideneacetone)dipalladium(0) (16 mg, 0.017 mmol) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (20 mg, 0.051 mmol) in dioxane (4 ml) were heated in a microwave reactor at 125° C. for 30 minutes. The reaction mixture was applied to an SCX ion exchange cartridge (Varian bond-elute) and washed with methanol and 2M ammonia in methanol. The combined basic fractions were concentrated in vacuo and the residue purified by mass directed autoprep HPLC to afford the title compound (E245). MS (ES+) m/e 512 [M+H]+.

後処理

  1. washThe reaction mixture was applied to an SCX ion exchange cartridge (Varian bond-elute)
  2. washwashed with methanol and 2M ammonia in methanol
  3. concentrationThe combined basic fractions were concentrated in vacuo
  4. customthe residue purified by mass

出典と根拠

ORDレコード
ord-6c0eb222b8b44af7b6c2cde901ab3206
出典データセット
uspto-grants-2008_06
特許番号
US07381728B2

反応ノート

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