Sodium Iodide → 6-Bromo-4-(5-{[(3R,5S)-3,5-dimethyl-4-(1-methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

HRID 520538노트

반응식

HRID 520538 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([C:20]2[O:21][C:22]([CH2:25]Br)=[N:23][N:24]=2)[CH:3]=1.[CH3:27][C@@H:28]1[CH2:33][NH:32][CH2:31][C@H:30]([CH3:34])[N:29]1[CH:35]([CH3:37])[CH3:36].CCN(C(C)C)C(C)C.[I-].[Na+]>C(#N)C.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:13])=[C:4]([C:20]2[O:21][C:22]([CH2:25][N:32]3[CH2:31][C@H:30]([CH3:34])[N:29]([CH:35]([CH3:37])[CH3:36])[C@H:28]([CH3:27])[CH2:33]3)=[N:23][N:24]=2)[CH:3]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 10583032(2R,6S)-2,6-Dimethyl-1-(1-methylethyl)piperazineHCID 667769666-Bromo-4-[5-(bromomethyl)-1,3,4-oxadiazol-2-yl]-1-(phenylsulfonyl)-1H-indazole

생성물 1

HCID 667785236-Bromo-4-(5-{[(3R,5S)-3,5-dimethyl-4-(1-methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

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온도
70 °C

실험 절차

6-Bromo-4-[5-(bromomethyl)-1,3,4-oxadiazol-2-yl]-1-(phenylsulfonyl)-1H-indazole (200 mg, 0.441 mmol) in acetonitrile (2 ml) was treated with (2R,6S)-2,6-dimethyl-1-(1-methylethyl)piperazine (138 mg, 0.883 mmol, see J. Med. Chem., 1999, 42, 1123-1144 for literature preparation), DIPEA (0.154 ml, 0.8825 mmol) and sodium iodide (66 mg, 0.44 mmol). The reaction mixture was heated at 70° C. for 5 h. The reaction mixture was then cooled, diluted with DCM and washed with an aqueous 2M HCl solution (5 ml). The organic layer was separated using a hydrophobic frit, washed with water and the solvent removed under a stream of nitrogen to give the title compound as a brown oil.

후처리

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with an aqueous 2M HCl solution (5 ml)
  3. customThe organic layer was separated
  4. washwashed with water
  5. customthe solvent removed under a stream of nitrogen

출처 및 근거

ORD 기록
ord-7c99a30ae6604787b0a1d09b9ec70fb7
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326987B2

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