Diisopropylethylamine → N-(3-{2-[4-(2-methyl-5-quinazolinyl)-1-piperazinyl]ethyl}phenyl)methanesulfonamide

HRID 1179626ノート

反応式

HRID 1179626 の反応式
[CH3:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:3]=1.CS(O[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:26]=1)(=O)=O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:23][CH2:24][C:25]3[CH:26]=[C:27]([NH:31][S:32]([CH3:35])(=[O:33])=[O:34])[CH:28]=[CH:29][CH:30]=3)[CH2:14][CH2:13]2)[N:3]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 57444358HCID 57444358、化合物HCID 574443592-{3-[(Methylsulfonyl)amino]phenyl}ethyl methanesulfonate

生成物 1

HCID 57444357N-(3-{2-[4-(2-methyl-5-quinazolinyl)-1-piperazinyl]ethyl}phenyl)methanesulfonamide収率 37.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-methyl-5-(1-piperazinyl)quinazoline (50 mg), 2-{3-[(methylsulfonyl)amino]phenyl}ethyl methanesulfonate (65 mg), diisopropylethylamine (192 μL) and DMF (0.5 mL) was heated to 100° C. in a sealed tube and stirred for 24 hours. The mixture was cooled to room temperature and partitioned between aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed (water, brine), dried (sodium sulfate) and concentrated in vacuo. The residue was purified by column chromatography [SiO2; DCM-MeOH: (100:0)→(95:5)] to give the title compound as a beige foam (35 mg).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between aqueous ammonium chloride solution and ethyl acetate
  3. washThe organic layer was washed (water, brine)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography [SiO2; DCM-MeOH: (100:0)→(95:5)]

出典と根拠

ORDレコード
ord-e9d2ec95763d4c97b00098cb96be5227
出典データセット
uspto-grants-2007_10
特許番号
US07279481B2

反応ノート

読み込み中…