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Tetrahydrofuran → 5-Chloro-3-(4,4-difluorocyclohexylmethyl)-2-trifluoromethylimidazo[1,2-a]pyridine-7-carboxylic acid

HRID 1468286
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인쇄 미리보기

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HRID 1468286 반응식
[Cl:1][C:2]1[N:7]2[C:8]([CH2:15][CH:16]3[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18][CH2:17]3)=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=[C:6]2[CH:5]=[C:4]([C:24]([O:26]CC)=[O:25])[CH:3]=1.C1COCC1.[OH-].[Na+]>O>[Cl:1][C:2]1[N:7]2[C:8]([CH2:15][CH:16]3[CH2:21][CH2:20][C:19]([F:22])([F:23])[CH2:18][CH2:17]3)=[C:9]([C:11]([F:12])([F:13])[F:14])[N:10]=[C:6]2[CH:5]=[C:4]([C:24]([OH:26])=[O:25])[CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86710093Ethyl 5-chloro-3-{(4,4-difluorocyclohexyl)methyl}-2-(trifluoromethyl)imidazo[1,2-a]pyridine-7-carboxylate

생성물 1

HCID 867100955-Chloro-3-(4,4-difluorocyclohexylmethyl)-2-trifluoromethylimidazo[1,2-a]pyridine-7-carboxylic acid수율 113.9%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

Ethyl 5-chloro-3-(4,4-difluorocyclohexylmethyl)-2-trifluoromethylimidazo[1,2-a]pyridine-7-carboxylate (62 mg, 0.146 mmol) obtained in step 2 was suspended in a mixed solvent of THF (2.0 mL) and water (2.0 mL), and the suspension was stirred under heat and reflux for 3 hours after adding sodium hydroxide (29 mg, 0.730 mmol). The reaction mixture was allowed to cool to room temperature, and the solvent was then evaporated under reduced pressure. The residue was extracted with water after adding chloroform. Following neutralization with 1 mol/L hydrochloric acid, the solvent was evaporated under reduced pressure. After adding a mixed solution of chloroform/methanol=4/1 to the residue, the insoluble matter was removed by filtration. The filtrate solvent was evaporated under reduced pressure to give a crude product of 5-chloro-3-(4,4-difluorocyclohexylmethyl)-2-trifluoromethylimidazo[1,2-a]pyridine-7-carboxylic acid (66 mg).

후처리

  1. temperatureunder heat
  2. temperaturereflux for 3 hours
  3. customthe solvent was then evaporated under reduced pressure
  4. extractionThe residue was extracted with water
  5. additionafter adding chloroform
  6. customthe solvent was evaporated under reduced pressure
  7. additionAfter adding a mixed solution of chloroform/methanol=4/1 to the residue
  8. customthe insoluble matter was removed by filtration
  9. customThe filtrate solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-b719afdb62274606acfc2098d2f4018a
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09000186B2

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