Hydrochloric Acid → 1-{[4-(3-acetylphenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylic acid

HRID 1257343노트

반응식

HRID 1257343 반응식
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH2:15][N:16]3[CH:20]=[C:19]([C:21]([O:23]CC)=[O:22])[CH:18]=[N:17]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C.O1CCCC1.[Cl-].[Na+].O>[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH2:15][N:16]3[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[N:17]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58127487ethyl 1-{[4-(3-acetylphenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylate

생성물 1

HCID 581278951-{[4-(3-acetylphenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylic acid수율 84%

시약·촉매·용매 2

HCID 21873804Tetrahydrofuran ethanol용매HCID 57417360Sodium chloride; water용매

실험 절차

To a mixed solution of the compound (188 mg, 0.53 mmol) obtained in Example 30d in ethanol-tetrahydrofuran (v/v=2/1) was added 2N aqueous sodium hydroxide solution (1.5 mL, 3.0 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 1N aqueous hydrochloric acid solution, saturated brine was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crude product was purified by recrystallization (ethyl acetate-hexane) to give the title compound (145 mg, 84%) as colorless crystals.

후처리

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by recrystallization (ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-616ff89e8b924bf7ab0e39fe3f9eb6d6
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461348B2

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