Potassium Hydroxide → HCID 49846225, 화합물

HRID 1930160노트

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HRID 1930160 반응식
[OH-].[K+].[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([F:24])=[CH:22][C:21]([CH:25]([CH3:30])[C:26]([O:28]C)=[O:27])=[CH:20][C:19]=3[F:31])=[CH:14][CH:13]=2)[C:9]([CH3:32])=[N:8][C:7]=1[CH3:33])(=[O:5])[NH2:4]>CC(O)(C)C>[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:23]([F:24])=[CH:22][C:21]([CH:25]([CH3:30])[C:26]([OH:28])=[O:27])=[CH:20][C:19]=3[F:31])=[CH:16][CH:17]=2)[C:9]([CH3:32])=[N:8][C:7]=1[CH3:33])(=[O:5])[NH2:4]

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 59627653HCID 59627653, 화합물2회

생성물 1

HCID 49846225HCID 49846225, 화합물수율 54.8%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

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온도
45 °C

실험 절차

Potassium hydroxide (0.396 g, 7.05 mmol) was added in one portion to methyl 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2,6-difluorobiphenyl-4-yl)propanoate (Intermediate 21-1; 1 g, 2.35 mmol) in t-BuOH (15.16 mL) at room temperature. The resulting solution was stirred at 45° C. for 5 hours, a precipitate formed. The reaction mixture was quenched with 2M HCl (5 mL), evaporated to dryness and redissolved in water (10 mL), filtered through nylon, washed with water and dried under vacuum to afford product as a white solid. The product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 50 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN/MeOH as eluents. Fractions containing the desired compound were evaporated to dryness to afford 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2,6-difluorobiphenyl-4-yl)propanoic acid (0.530 g, 54.8%) as a white powder.

후처리

  1. customa precipitate formed
  2. customThe reaction mixture was quenched with 2M HCl (5 mL)
  3. customevaporated to dryness
  4. dissolutionredissolved in water (10 mL)
  5. filtrationfiltered through nylon
  6. washwashed with water
  7. customdried under vacuum
  8. customto afford product as a white solid
  9. customThe product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 50 mm diameter, 150 mm length)
  10. additionFractions containing the desired compound
  11. customwere evaporated to dryness

출처 및 근거

ORD 기록
ord-87bd6f69b90c4c559f96a1a29b8722f8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188092B2

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