2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → N-[2-(Methyloxy)-5-(cis-3,4,5-trimethyl-1-piperazinyl)phenyl]-4-(2-thienyl)benzenesulfonamide

HRID 130471

反応式

HRID 130471 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:7]=1.[CH3:25][N:26]1[C@H:31]([CH3:32])[CH2:30][NH:29][CH2:28][C@@H:27]1[CH3:33].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]>[CH3:24][O:23][C:5]1[CH:4]=[CH:3][C:2]([N:29]2[CH2:30][C@H:31]([CH3:32])[N:26]([CH3:25])[C@H:27]([CH3:33])[CH2:28]2)=[CH:7][C:6]=1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10]

参加物

7

反応物 4

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 30720221(2R,6S)-1,2,6-TrimethylpiperazineHCID 69197888N-[5-Bromo-2-(methyloxy)phenyl]-4-(2-thienyl)benzenesulfonamide

生成物 1

HCID 59007104N-[2-(Methyloxy)-5-(cis-3,4,5-trimethyl-1-piperazinyl)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 (200 mg, 0.47 mmol), cis-1,2,6-trimethyl piperazine (118 mg, 0.94 mmol), sodium tert-butoxide (90 mg, 0.94 mmol), tris(dibenzylideneacetone)dipalladium(0) (22 mg, 0.024 mmol) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (28 mg, 0.071 mmol) in dioxane (10 ml) was heated at reflux for 16 hours. After cooling to room temperature the solution was concentrated in vacuo. The residue 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 to afford the title product (E277). MS (ES+) 472 [M+H]+.

後処理

  1. temperatureat reflux for 16 hours
  2. concentrationwas concentrated in vacuo
  3. washThe residue was applied to an SCX ion exchange cartridge (Varian bond-elute)
  4. washwashed with methanol and 2M ammonia in methanol
  5. concentrationThe combined basic fractions were concentrated in vacuo
  6. customthe residue purified by mass

出典と根拠

ORDレコード
ord-3ed538457f03455e999eb27dbda60181
出典データセット
uspto-grants-2008_06
特許番号
US07381728B2

関連ノート

読み込み中…