Pyridine → 1-[5-(Methanesulfonamido)indole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

HRID 1449752ノート

反応式

HRID 1449752 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]3[C:24]([NH:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:15][CH2:14]1)=[O:12])=[CH:5]2.N1C=CC=CC=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl.O>[CH3:37][S:38]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]3[C:24]([NH:25][C:26]([CH3:29])([CH3:30])[CH2:27][CH3:28])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:15][CH2:14]1)=[O:12])=[CH:5]2)(=[O:40])=[O:39]

参加物

6

反応物 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 214776001-[5-Aminoindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

生成物 1

HCID 214776751-[5-(Methanesulfonamido)indole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 1-[5-aminoindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine (EXAMPLE 41, 300 mg) in dry methylene chloride (6 ml) under nitrogen is added pyridine (119 μl) and methanesulfonyl chloride (57 μl). The mixture is stirred at 20°-25° for 24 hr and then diluted with methylene chloride (20 ml) and water (8 ml). The layers are separated and the organic phase is washed with saline (8 ml), dried over sodium sulfate, and concentrated to give a solid which is then chromatographed on silica gel (230-400 mesh, 34 g, 5-6 psi), eluting with methanol/chloroform (2.5/97.5). Pooling of the appropriate fractions, concentration to a solid, and recrystallization from chloroform gives the title compound, mp 232°-233° (decomp).

後処理

  1. customThe layers are separated
  2. washthe organic phase is washed with saline (8 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a solid which
  6. customis then chromatographed on silica gel (230-400 mesh, 34 g, 5-6 psi)
  7. washeluting with methanol/chloroform (2.5/97.5)
  8. concentrationPooling of the appropriate fractions, concentration
  9. customto a solid, and recrystallization from chloroform

出典と根拠

ORDレコード
ord-348e849b344f4e3ab5c75ea0b6c8b5bc
出典データセット
uspto-grants-1997_02
特許番号
US05599930

反応ノート

読み込み中…