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

HRID 10329ノート

反応式

HRID 10329 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-950eac8099204e9080cda488ff8ca284
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

反応ノート

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