Oxalyl chloride → 1-Cyclopropyl-3-(2,6-dichloro-5-fluoro-pyridine-3-carbonyl)urea

HRID 10329노트

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HRID 10329 반응식
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:13](Cl)(=[O:17])C(Cl)=O.[CH:19]1([NH2:22])[CH2:21][CH2:20]1>ClCCl>[CH:19]1([NH:22][C:13]([NH:6][C:4]([C:3]2[C:2]([Cl:1])=[N:10][C:9]([Cl:11])=[C:8]([F:12])[CH:7]=2)=[O:5])=[O:17])[CH2:21][CH2:20]1

참가 물질

5

반응물 3

HCID 65578Oxalyl chlorideHCID 69828CyclopropylamineHCID 27740222,6-Dichloro-5-fluoronicotinamide

생성물 1

HCID 219794261-Cyclopropyl-3-(2,6-dichloro-5-fluoro-pyridine-3-carbonyl)urea수율 98.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-20 °C

실험 절차

A solution of 5.8 g (27.8 mmol) of 2,6-dichloro-5-fluoronicotinamide (Chem. Pharm. Bull., 1987; 35:2280) in 60 mL of dichloromethane is treated dropwise with 5.1 g (40 mmol) of oxalyl chloride, and the reaction mixture is heated at reflux for 18 hours. The solvent is removed in vacuo, and the residue is dissolved in 50 mL of dichloromethane, which is also removed in vacuo. The residue is dissolved in 50 mL of dichloromethane, cooled to −20° C. and treated dropwise with 2.28 g (40 mmol) of cyclopropylamine. The reaction mixture is stirred at −20° to −10° C. for ½ hour, then allowed to come to room temperature over 2 hours. The solvent is removed in vacuo and the residue is triturated with 25 mL of dichloromethane, which is also removed in vacuo to give 8.0 g of the title compound, mp 171–173° C.

후처리

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent is removed in vacuo
  4. dissolutionthe residue is dissolved in 50 mL of dichloromethane
  5. customwhich is also removed in vacuo
  6. dissolutionThe residue is dissolved in 50 mL of dichloromethane
  7. waitto come to room temperature over 2 hours
  8. customThe solvent is removed in vacuo
  9. customthe residue is triturated with 25 mL of dichloromethane, which
  10. customis also removed in vacuo

출처 및 근거

ORD 기록
ord-950eac8099204e9080cda488ff8ca284
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094780B1

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