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

HRID 1624094노트

반응식

HRID 1624094 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

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온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f097373378b44bee91a723e585e3ad13
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778964B2

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