Tetrahydrofuran → 3-(4,4-Difluorocyclohexylmethyl)-6-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridine-7-carboxylic acid

HRID 1468294노트

반응식

HRID 1468294 반응식
[F:1][C:2]1([F:28])[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[N:13]3[CH:14]=[C:15]([O:22][CH3:23])[C:16]([C:18]([O:20]C)=[O:19])=[CH:17][C:12]3=[N:11][C:10]=2[C:24]([F:27])([F:26])[F:25])[CH2:4][CH2:3]1.C1COCC1.[OH-].[Na+]>O>[F:28][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([CH2:8][C:9]2[N:13]3[CH:14]=[C:15]([O:22][CH3:23])[C:16]([C:18]([OH:20])=[O:19])=[CH:17][C:12]3=[N:11][C:10]=2[C:24]([F:25])([F:26])[F:27])[CH2:6][CH2:7]1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86710108Methyl 3-(4,4-difluorocyclohexylmethyl)-6-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridine-7-carboxylate

생성물 1

HCID 867101093-(4,4-Difluorocyclohexylmethyl)-6-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridine-7-carboxylic acid수율 99%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Methyl 3-(4,4-difluorocyclohexylmethyl)-6-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridine-7-carboxylate (23 mg, 0.057 mmol) obtained in step 4 was suspended in a mixed solvent of THF (1.0 mL) and water (1.0 mL), and the suspension was stirred under heat and reflux for 3 hours after adding sodium hydroxide (11 mg, 0.283 mmol). The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was extracted with water after adding chloroform, then neutralized 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 3-(4,4-difluorocyclohexylmethyl)-6-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridine-7-carboxylic acid (22.0 mg, yield 99%).

후처리

  1. temperatureunder heat
  2. temperaturereflux for 3 hours
  3. customthe solvent was 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-85b9a7cd0b624327983a367d575de834
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000186B2

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