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

HRID 729415노트

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HRID 729415 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

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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-a5f9f19f3f9c4517aa86bd278e129a02
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582627B2

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