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

HRID 72484
ノート
印刷プレビュー

反応式

HRID 72484 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

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

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6ac1b0b128a04874a890d135fbd1aa6a
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08828987B2

反応ノート

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