Dimethylformamide → HCID 136337085、化合物

HRID 2079143ノート

反応式

HRID 2079143 の反応式
COC(=O)N=[C:5](SC)[C:6]([C:20]1[CH:25]=[C:24]([CH2:26][O:27][CH3:28])[C:23]([O:29][CH3:30])=[C:22]([O:31][CH3:32])[CH:21]=1)=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1.[NH:36]([C:38]1[N:43]=[CH:42]C=[CH:40][N:39]=1)[NH2:37].C(N(CC)CC)C.[CH3:51][N:52]([CH:54]=[O:55])C>>[CH3:32][O:31][C:22]1[CH:21]=[C:20]([CH:6]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:18]=[C:17]([CH3:19])[O:16][N:15]=3)=[CH:12][CH:13]=2)[C:5]2[CH:40]=[N:39][C:38]([N:36]3[C:54](=[O:55])[NH:52][CH:51]=[N:37]3)=[N:43][CH:42]=2)[CH:25]=[C:24]([CH2:26][O:27][CH3:28])[C:23]=1[O:29][CH3:30]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 3465582-HydrazinylpyrimidineHCID 72312817HCID 72312817、化合物

生成物 1

HCID 136337085HCID 136337085、化合物

反応条件

温度
85 °C

実験手順

To a solution of 169 mg of [2-(3,4-dimethoxy-5-methoxymethylphenyl) -2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester in 2 ml of DMF there were added 40 mg of 2-hydrazinopyrimidine and 50 μl of triethylamine, and the mixture was stirred overnight at 85° C. under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 3 ml of methanol and 0.3 ml of acetic acid. After adding 100 mg of sodium cyanotrihydroborate to the solution, the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate) to give 5-{(3,4-dimethoxy-5-methoxymethylphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}pyrimidin-2-yl-2,4-dihydro-[1,2,4]triazol-3-one (89 mg) as a light brown solid.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in 3 ml of methanol
  3. additionAfter adding 100 mg of sodium cyanotrihydroborate to the solution
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. additionWater was added to the reaction mixture and extraction
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationThe desiccating agent was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate)

出典と根拠

ORDレコード
ord-a6773f9dcfe448e8b050c5d2193477a5
出典データセット
uspto-grants-2011_04
特許番号
US07928228B2

反応ノート

読み込み中…