Pyridine → 3-(5-bromo-2-fluorobenzoylamino)pyrazine-2-carboxylic Acid Methyl Ester

HRID 928260ノート

反応式

HRID 928260 の反応式
N1C=CC=CC=1.[CH3:7][O:8][C:9]([C:11]1[C:16]([NH2:17])=[N:15][CH:14]=[CH:13][N:12]=1)=[O:10].[Br:18][C:19]1[CH:20]=[CH:21][C:22]([F:28])=[C:23]([CH:27]=1)[C:24](Cl)=[O:25]>C(Cl)Cl>[CH3:7][O:8][C:9]([C:11]1[C:16]([NH:17][C:24](=[O:25])[C:23]2[CH:27]=[C:19]([Br:18])[CH:20]=[CH:21][C:22]=2[F:28])=[N:15][CH:14]=[CH:13][N:12]=1)=[O:10]

参加物

5

反応物 3

HCID 1049PyridineHCID 72669Methyl 3-aminopyrazinecarboxylateHCID 219426655-Bromo-2-fluorobenzoyl chloride

生成物 1

HCID 577423823-(5-bromo-2-fluorobenzoylamino)pyrazine-2-carboxylic Acid Methyl Ester収率 74.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

Pyridine (7.75 g, 98.0 mmol) was added at 0° C. under N2 to a solution of 3-amino-pyrazine-2-carboxylic acid methyl ester 101 (1.5 g, 9.80 mmol) and 5-bromo-2-fluorobenzoylchloride (9.45 g, 49.0 mmol) in CH2Cl2. The reaction mixture was warmed at 40° C. for 4 h, then cooled down at room temperature. The reaction mixture was quenched with 20 mL of ethanol, evaporated, partitioned between CH2Cl2 and 1N NaHCO3, dried (Na2SO4) and evaporated. The crude material was triturated in EtOH, filtered, washed with EtOH and ether to give 2.6 g of 3-(5-bromo-2-fluorobenzoyl-amino)pyrazine-2-carboxylic acid methyl ester 102 as a white powder (LCMS analysis).

後処理

  1. temperaturecooled down at room temperature
  2. customThe reaction mixture was quenched with 20 mL of ethanol
  3. customevaporated
  4. custompartitioned between CH2Cl2 and 1N NaHCO3
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude material was triturated in EtOH
  8. filtrationfiltered
  9. washwashed with EtOH and ether

出典と根拠

ORDレコード
ord-0dbe4e01e51f4585b612c989d975e450
出典データセット
uspto-grants-2016_03
特許番号
US09290502B2

反応ノート

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