Hydrochloric Acid → 5-Methyl-6-((2,2,2-trifluoroethyl)amino)nicotinic acid

HRID 715412ノート

反応式

HRID 715412 の反応式
F[C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][N:3]=1.[F:13][C:14]([F:18])([F:17])[CH2:15][NH2:16].Cl>CN1CCCC1=O.CO.[OH-].[Na+]>[CH3:12][C:11]1[C:2]([NH:16][CH2:15][C:14]([F:18])([F:17])[F:13])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([OH:8])=[O:7]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 53419770Methyl 6-fluoro-5-methylpyridine-3-carboxylate

生成物 1

HCID 898739845-Methyl-6-((2,2,2-trifluoroethyl)amino)nicotinic acid収率 32%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 13387N-methyl-2-pyrrolidone溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
220 °C

実験手順

A mixture of methyl 6-fluoro-5-methylnicotinate (2.00 g, 11.8 mmol, Step-1 of Amine-36) and 2,2,2-trifluoroethanamine (9.37 g, 95 mmol) in N-methylpyrrolidone (24 mL) is stirred at 220° C. for 2.5 hours under microwave irradiation. The mixture is diluted with MeOH (30 mL), and 2 M aqueous sodium hydroxide solution (15 mL) is added to the mixture. After stirring at 50° C. for 1 hour, the mixture is acidified by 2 M hydrochloric acid, and extracted with EtOAc/hexane (100 mL×3). The combined organic layer is washed with water (100 mL), and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is crystallized from diisopropyl ether to give 884 mg (32%) of the title compound as a pale pink solid.

後処理

  1. additionis added to the mixture
  2. stirringAfter stirring at 50° C. for 1 hour
  3. extractionextracted with EtOAc/hexane (100 mL×3)
  4. washThe combined organic layer is washed with water (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is crystallized from diisopropyl ether

出典と根拠

ORDレコード
ord-09c35eb43bf841bbbfdf52a0ad8b0676
出典データセット
uspto-grants-2015_11
特許番号
US09187475B2

反応ノート

読み込み中…