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Sodium Hydroxide → 5-Fluoro-2-(3-((4-fluoro-2-methylphenyl)amino)azetidin-1-yl)nicotinic acid

HRID 72484
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HRID 72484 반응식
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:13][CH:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[CH2:15]2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 67958301Methyl 5-fluoro-2-(3-((4-fluoro-2-methylphenyl)amino)azetidin-1-yl)nicotinate

생성물 1

HCID 679581095-Fluoro-2-(3-((4-fluoro-2-methylphenyl)amino)azetidin-1-yl)nicotinic acid수율 97.4%

시약·촉매·용매 1

HCID 218864351,4-Dioxane--water (1/1)용매

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온도
60 °C

실험 절차

To a solution of methyl 5-fluoro-2-(3-((4-fluoro-2-methylphenyl)amino)azetidin-1-yl)nicotinate (D90) (150 mg, 0.450 mmol) in 1,4-dioxane/water (3 ml/1 ml), 1M NaOH (0.675 ml, 0.657 mmol) was added and the resulting mixture was stirred 2 h at 60° C. Organic solvent was evaporated. The remaining aqueous were washed with dichloromethane (5 ml) then acidified to pH2 by addition of 2M HCl and extracted with ethylacetate (3×20 ml). Collected organics, after solvent evaporation afforded the title compound (D135) (140 mg).

후처리

  1. customOrganic solvent was evaporated
  2. washThe remaining aqueous were washed with dichloromethane (5 ml)
  3. additionthen acidified to pH2 by addition of 2M HCl
  4. extractionextracted with ethylacetate (3×20 ml)
  5. customCollected organics, after solvent evaporation

출처 및 근거

ORD 기록
ord-6ac1b0b128a04874a890d135fbd1aa6a
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08828987B2

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