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Methanol → HCID 90304553、化合物

HRID 62457
ノート
印刷プレビュー

反応式

HRID 62457 の反応式
[C:1]([CH2:3][CH2:4][CH:5]([C:10]1[N:14]2[CH:15]=[CH:16][N:17]=[C:18]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=3[O:29][CH3:30])[C:13]2=[C:12]([C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)[N:11]=1)[C:6]([O:8]C)=O)#[N:2].CO>CCO.[Ni]>[CH3:30][O:29][C:22]1[CH:23]=[C:24]([O:27][CH3:28])[CH:25]=[CH:26][C:21]=1[CH2:20][NH:19][C:18]1[C:13]2[N:14]([C:10]([CH:5]3[CH2:4][CH2:3][CH2:1][NH:2][C:6]3=[O:8])=[N:11][C:12]=2[C:31]2[CH:32]=[CH:33][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:39][CH:40]=2)[CH:15]=[CH:16][N:17]=1
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

5

反応物 2

HCID 887MethanolHCID 90304033Methyl 4-(3-(4-cyano-1-methoxy-1-oxobutan-2-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate

生成物 1

HCID 90304553HCID 90304553、化合物収率 40.4%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

反応条件

温度
75 °C

実験手順

To a solution of methyl 4-(3-(4-cyano-1-methoxy-1-oxobutan-2-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate (12 g, 22.1 mmol) in EtOH (350 mL) was added Ra—Ni (24 g) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 (50 psi) at 75° C. for 7 hours. The reaction was complete detected by LCMS. The suspension was filtered through a pad of Celite and the pad was washed with EtOH (20 mL×3). The combined filtrates were concentrated. The residue was purified by column chromatography on silica gel eluted with DCM:MeOH=30:1 to give methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-oxopiperidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)benzoate (4.6 g, yield 40%).

後処理

  1. customThe suspension was degassed under vacuum
  2. custompurged with H2 several times
  3. filtrationThe suspension was filtered through a pad of Celite
  4. washthe pad was washed with EtOH (20 mL×3)
  5. concentrationThe combined filtrates were concentrated
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluted with DCM

出典と根拠

ORDレコード
ord-9451584972f74532876f40a018e6ef07
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09446130B2

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