Hydrochloric Acid → 8-[(2,6-Difluorobenzyl)oxy]-2-methyl-6-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1844145노트

반응식

HRID 1844145 반응식
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:17]([C:21]([O:23]CC)=[O:22])=[C:18]([CH3:20])[N:19]=2)[CH:9]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=1.[OH-].[Li+].Cl>C1COCC1.CO>[F:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:17]([C:21]([OH:23])=[O:22])=[C:18]([CH3:20])[N:19]=2)[CH:9]=[C:10]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[CH:11]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86718167Ethyl 8-[(2,6-difluorobenzyl)oxy]-2-methyl-6-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylate

생성물 1

HCID 867181688-[(2,6-Difluorobenzyl)oxy]-2-methyl-6-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylic acid

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

90 mg of ethyl 8-[(2,6-difluorobenzyl)oxy]-2-methyl-6-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylate (Example 32A; 0.217 mmol, 1 equivalent) were dissolved in 6 ml of THF/methanol 5:1, 1.1 ml of 1N aqueous lithium hydroxide solution (1.1 mmol, 5 equivalents) were added and the mixture was warmed to 40° C. and stirred at this temperature for 20 h. The mixture was cooled, acidified to pH 4 with 6 N hydrochloric acid and concentrated. Water was added to the solid formed and the product was triturated, filtered off with suction, washed with water and dried under reduced pressure. This gave 87 mg of the title compound (93% of theory).

후처리

  1. additionwere added
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. additionWater was added to the solid
  5. customformed
  6. customthe product was triturated
  7. filtrationfiltered off with suction
  8. washwashed with water
  9. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-026fbe32981145d0b2868102c3dd17a4
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946215B2

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