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

HRID 1468294ノート

反応式

HRID 1468294 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-85b9a7cd0b624327983a367d575de834
出典データセット
uspto-grants-2015_04
特許番号
US09000186B2

反応ノート

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