Hydrochloric Acid → 1-[(7-{[2,4-bis(trifluoromethyl)benzyl]oxy}-5-fluoro-2H-chromen-3-yl)methyl]-1H-pyrazole-4-carboxylic acid

HRID 217474노트

반응식

HRID 217474 반응식
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:4]=1[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:17][N:18]3[CH:22]=[C:21]([C:23]([O:25]CC)=[O:24])[CH:20]=[N:19]3)[CH2:13][O:14]2)=[C:9]([F:28])[CH:8]=1.[OH-].[Na+].Cl>CCO.C1COCC1>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:32]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:30]=[CH:29][C:4]=1[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:17][N:18]3[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[CH:20]=[N:19]3)[CH2:13][O:14]2)=[C:9]([F:28])[CH:8]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86657650ethyl 1-[(7-{[2,4-bis(trifluoromethyl)benzyl]oxy}-5-fluoro-2H-chromen-3-yl)methyl]-1H-pyrazole-4-carboxylate

생성물 1

HCID 866576561-[(7-{[2,4-bis(trifluoromethyl)benzyl]oxy}-5-fluoro-2H-chromen-3-yl)methyl]-1H-pyrazole-4-carboxylic acid수율 74.9%

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

A solution of ethyl 1-[(7-{[2,4-bis(trifluoromethyl)benzyl]oxy}-5-fluoro-2H-chromen-3-yl)methyl]-1H-pyrazole-4-carboxylate (100 mg) and a 1 M aqueous NaOH solution (0.55 mL) in EtOH/THF (3 mL/1 mL) was stirred at 100° C. for 2 hours, neutralized with 1 M HCl, and extracted with chloroform. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10) and the obtained solid was washed with IPE to obtain 1-[(7-{[2,4-bis(trifluoromethyl)benzyl]oxy}-5-fluoro-2H-chromen-3-yl)methyl]-1H-pyrazole-4-carboxylic acid (71 mg) as a white solid.

후처리

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10)
  6. washthe obtained solid was washed with IPE

출처 및 근거

ORD 기록
ord-5a30d75f1b64458da5443869b1378b16
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193378B2

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