Hydrochloric Acid → 6-Cyclopropyl-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1844152ノート

反応式

HRID 1844152 の反応式
[CH:1]1([C:4]2[CH:5]=[C:6]([O:19][CH2:20][C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[F:28])[C:7]3[N:8]([C:10]([C:14]([O:16]CC)=[O:15])=[C:11]([CH3:13])[N:12]=3)[CH:9]=2)[CH2:3][CH2:2]1.[OH-].[Li+].Cl>O1CCCC1.CO>[CH:1]1([C:4]2[CH:5]=[C:6]([O:19][CH2:20][C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[F:28])[C:7]3[N:8]([C:10]([C:14]([OH:16])=[O:15])=[C:11]([CH3:13])[N:12]=3)[CH:9]=2)[CH2:2][CH2:3]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86718174Ethyl 6-cyclopropyl-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate

生成物 1

HCID 867181756-Cyclopropyl-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

470 mg of ethyl 6-cyclopropyl-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate (Example 41A) were initially charged in 36 ml of tetrahydrofuran/methanol 5:1, and 6.1 ml of 1N aqueous lithium hydroxide solution were added. The mixture was stirred at 40° C. for 4 h and then acidified with 6 N hydrochloric acid and concentrated. The residue was taken up in water and repeatedly extracted with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried with magnesium sulphate and filtered, and the filtrate was concentrated. This gave 470 mg of the desired product (90% pure; 97% of theory) which was reacted without further purification.

後処理

  1. additionwere added
  2. concentrationconcentrated
  3. extractionrepeatedly extracted with dichloromethane
  4. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried with magnesium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThis gave 470 mg of the desired product (90% pure; 97% of theory) which was reacted without further purification

出典と根拠

ORDレコード
ord-51125c6f1e7a45ecb3054827232c4256
出典データセット
uspto-grants-2015_02
特許番号
US08946215B2

反応ノート

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