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Lithium hydroxide, monohydrate → 1-[4'-(2"-Ethyl-5",7"-dimethylimidazo[4,5-b]pyridin-3-yl)methylphenyl]cyclopent-3-ene-1-carboxylic acid

HRID 1463531
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HRID 1463531 반응식
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3([C:26]([O:28]C)=[O:27])[CH2:25][CH:24]=[CH:23][CH2:22]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].O.[OH-].[Li+]>CO.O>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3([C:26]([OH:28])=[O:27])[CH2:25][CH:24]=[CH:23][CH2:22]3)=[CH:19][CH:20]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 86747731Methyl 1-[4'-(2"-ethyl-5",7"-dimethylimidazo[4,5-b]pyridin-3-yl)methylphenyl]cyclopent-3-ene-1-carboxylate

생성물 1

HCID 99295271-[4'-(2"-Ethyl-5",7"-dimethylimidazo[4,5-b]pyridin-3-yl)methylphenyl]cyclopent-3-ene-1-carboxylic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of the product of Step 5, above (5.76 g, 14.9 mmol) and lithium hydroxide monohydrate (6.23 g, 148 mmol) in 148 ml of methanol and 148 ml of water was heated at reflux for 2 hours. The reaction was then concentrated in vacuo, the residue was taken up in water and the pH was adjusted to 4 with concentrated HCl when the title compound precipitated as a colorless solid which was filtered off, dried in vacuo and recrystallized first from ethyl acetate/methanol, then from methanol to yield 1.9 g of title compound which was contaminated with 2.5% of 1-[4'-(2"-ethyl-5",7"-dimethylimidazo[4,5-b]pyridin-3-yl)methylphenyl]-2-vinylcyclopropane-1-carboxylic acid. Another recrystallization from methanol yielded 1.5 g of title compound, mp 232°-233° C., now about 98.3% pure, as determined by reverse-phase HPLC using a C-18 Beckman 25 cm long column and 30% pH 2.3 phosphate buffer in acetonitrile as eluant.

후처리

  1. temperatureat reflux for 2 hours
  2. concentrationThe reaction was then concentrated in vacuo
  3. customprecipitated as a colorless solid which
  4. filtrationwas filtered off
  5. customdried in vacuo
  6. customrecrystallized first from ethyl acetate/methanol

출처 및 근거

ORD 기록
ord-9c378bc1889041eab06f2abf3b238525
출처 데이터셋
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05300668

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