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Methanesulfonyl chloride → {2-[3-(4-methanesulfonyl-piperazin-1-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone

HRID 1677484
ノート
印刷プレビュー

反応式

HRID 1677484 の反応式
[CH3:1][C:2]1([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:20]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1>[CH3:31][S:32]([N:28]1[CH2:29][CH2:30][N:25]([C:21]2[CH:20]=[C:19]([C:16]3[N:17]=[C:18]4[C:10]([C:8]([C:2]5([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]5)=[O:9])=[CH:11][NH:12][C:13]4=[N:14][CH:15]=3)[CH:24]=[CH:23][CH:22]=2)[CH2:26][CH2:27]1)(=[O:34])=[O:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 59540704(1-methyl-cyclohexyl)-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

生成物 1

HCID 59540692{2-[3-(4-methanesulfonyl-piperazin-1-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone収率 22.7%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

A solution of (1-methyl-cyclohexyl)-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (135 mg, 0.33 mmol) in pyridine (3 ml), at 0° C., was treated with methane sulfonyl chloride (0.03 ml, 0.367 mmol). The reaction mixture was allowed to stir at 0° C. for 1.5 hours, and then room temperature for 16 hours. The reaction mixture was poured onto ice cold 1N HCl and extracted with DCM. The organic layers were collected, dried over MgSO4, filtered and concentrated giving a yellow film. The crude product was purified by preparative thin layer chromatography using 3% [5% NH4OH:MeOH]/DCM as eluant providing 36 mg (22%) of {2-[3-(4-methanesulfonyl-piperazin-1-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone as an off white solid. MP 230-231° C., M+H=482.

後処理

  1. waitroom temperature for 16 hours
  2. additionThe reaction mixture was poured onto ice cold 1N HCl
  3. extractionextracted with DCM
  4. customThe organic layers were collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customgiving a yellow film
  9. customThe crude product was purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-4a6e6e95bcd64ff7b094d9cf4c0e4368
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08008298B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート