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

HRID 130471

반응식

HRID 130471 반응식
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]

참가 물질

7

반응물 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

생성물 1

HCID 59007104N-[2-(Methyloxy)-5-(cis-3,4,5-trimethyl-1-piperazinyl)phenyl]-4-(2-thienyl)benzenesulfonamide

시약·촉매·용매 2

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

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-3ed538457f03455e999eb27dbda60181
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381728B2

연결된 노트

불러오는 중…