Sodium Hydroxide → 1-[5-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)thiophen-2-yl]cyclopent-3-ene carboxylic acid

HRID 481391노트

반응식

HRID 481391 반응식
C([O:3][C:4]([C:6]1([C:11]2[S:12][C:13]([CH2:16][N:17]3[C:21]4=[N:22][C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]4[N:19]=[C:18]3[CH2:28][CH3:29])=[CH:14][CH:15]=2)[CH2:10][CH:9]=[CH:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[CH2:28]([C:18]1[N:17]([CH2:16][C:13]2[S:12][C:11]([C:6]3([C:4]([OH:5])=[O:3])[CH2:10][CH:9]=[CH:8][CH2:7]3)=[CH:15][CH:14]=2)[C:21]2=[N:22][C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]2[N:19]=1)[CH3:29]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 684276321-[5-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)-thiophen-2-yl]cyclopent-3ene carboxylic acid ethyl ester2회

생성물 1

HCID 190662441-[5-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)thiophen-2-yl]cyclopent-3-ene carboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
80 °C

실험 절차

To a solution of the product of Step 5, above (6), in methanol was added an excess of 2N NaOH. The reaction mixture was heated to 80° C. for 1 hour, cooled to room temperature and the solvent evaporated. Water was added to the residue and the solution was extracted 2 times with EtOAc. The aqueous layer was acidified with 10% HCl and the resultant white suspension was extracted 2 times with EtOAc. The organics were dried over MgSO4, filtered and concentrated to a solid. The solid was crystallized from EtOAc to yield the title compound (8).

후처리

  1. temperaturecooled to room temperature
  2. customthe solvent evaporated
  3. additionWater was added to the residue
  4. extractionthe solution was extracted 2 times with EtOAc
  5. extractionthe resultant white suspension was extracted 2 times with EtOAc
  6. dry with materialThe organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a solid
  9. customThe solid was crystallized from EtOAc

출처 및 근거

ORD 기록
ord-9031c5cc868a412a889a909539eeb33c
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789415

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