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

HRID 884393

반응식

HRID 884393 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

4-[4-(4-Carboxy-phenyl)-5-methyl-thiazol-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 under vacuum, 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%).

후처리

  1. customThe solvent was then removed under vacuum
  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

출처 및 근거

ORD 기록
ord-7db112fad9834e48814cc8dffc0a56b0
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242119B2

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