Sodium hydride → (E)-tert-butyl 5-(2-methyl-5-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamido)styryl)pyrazin-2-ylcarbamate

HRID 2199316ノート

反応式

HRID 2199316 の反応式
C(OP([CH2:9][C:10]1[N:11]=[CH:12][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14][CH:15]=1)(OCC)=O)C.[H-].[Na+].[CH:26]([C:28]1[CH:29]=[C:30]([NH:35][C:36](=[O:55])[C:37]2[CH:42]=[CH:41][C:40]([CH2:43][N:44]3[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]3)=[C:39]([C:51]([F:54])([F:53])[F:52])[CH:38]=2)[CH:31]=[CH:32][C:33]=1[CH3:34])=O>CN(C=O)C>[CH3:34][C:33]1[CH:32]=[CH:31][C:30]([NH:35][C:36](=[O:55])[C:37]2[CH:42]=[CH:41][C:40]([CH2:43][N:44]3[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]3)=[C:39]([C:51]([F:53])([F:54])[F:52])[CH:38]=2)=[CH:29][C:28]=1/[CH:26]=[CH:9]/[C:10]1[N:11]=[CH:12][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[N:14][CH:15]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 59649414HCID 59649414、化合物HCID 86676738HCID 86676738、化合物

生成物 1

HCID 68304566(E)-tert-butyl 5-(2-methyl-5-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamido)styryl)pyrazin-2-ylcarbamate収率 65.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

tert-butyl 5-((diethoxyphosphoryl)methyl)pyrazin-2-ylcarbamate (35 mg, 0.10 mmol) in dried DMF (0.5 mL) was added NaH (5 mg, 0.12 mmol) at 0° C. After 20 minutes, a solution N-(3-formyl-4-methylphenyl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide (44 mg, 0.10 mmol) in dried DMF (0.5 mL) was added slowly into the reaction mixture. The reaction mixture was stirred overnight at room temperature and quenched by adding water. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (3% to 7% MeOH/CH2Cl2) as a solvent to afford title compound (40 mg, 64% yield). MS m/z: 611 [M+1].

後処理

  1. customquenched
  2. additionby adding water
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4, celite
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-8494a39618ef4984bdebd81290958d23
出典データセット
uspto-grants-2016_06
特許番号
US09358231B2

反応ノート

読み込み中…