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

HRID 928260노트

반응식

HRID 928260 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0dbe4e01e51f4585b612c989d975e450
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290502B2

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