Formaldehyde → 4-[5-Methyl-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]benzoic acid

HRID 1258485ノート

反応式

HRID 1258485 の反応式
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]([CH3:28])=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CC(O)=O.C(O[Na])(C)=O.C=O.[BH3-]C#N.[Na+]>Cl.O1CCOCC1>[CH3:28][C:16]1[S:15][C:14]([N:11]2[CH2:10][CH2:9][N:8]([CH3:6])[CH2:13][CH2:12]2)=[N:18][C:17]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 575519874-[4-(4-Carboxyphenyl)-5-methylthiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl esterHCID 178476574sodium;acetic acid;acetate

生成物 1

HCID 598073194-[5-Methyl-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]benzoic acid収率 95.7%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

4-[4-(4-Carboxyphenyl)-5-methylthiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.421 mmol) was dissolved in 4M HCl in 1,4-dioxane, and stirred at room temperature for 1 h. The solvent was then removed in vacuo, and the residue 4-(5-methyl-2-piperazin-1-yl-thiazol-4-yl)-benzoic acid was suspended in methanol (10 mL) and treated with AcOH/AcONa buffer (pH ˜5.5, 5 mL), and formaldehyde (0.547 mmol). The reaction mixture was stirred at room temperature for 1 h, then treated with NaCNBH3 (0.547 mmol) and stirred at room temperature overnight. The solvent was then removed under vacuum, and the residue was purified by column chromatography to afford the title compound (0.403 mmol, 95%).

後処理

  1. customThe solvent was then removed in vacuo
  2. stirringThe reaction mixture was stirred at room temperature for 1 h
  3. stirringstirred at room temperature overnight
  4. customThe solvent was then removed under vacuum
  5. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-56ccfb16928a4d1f865f9ae8ae6ccb85
出典データセット
uspto-grants-2013_06
特許番号
US08466158B2

反応ノート

読み込み中…