4-Fluoroaniline → 4-(3-Fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridine-2-carboxamide

HRID 2066255ノート

反応式

HRID 2066255 の反応式
[C:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3([C:23]([OH:25])=O)[CH2:22][CH2:21]3)=[O:19])=[C:13]([F:26])[CH:12]=2)[CH:7]=[CH:6][N:5]=1)(=[O:3])[NH2:2].[F:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>O1CCCC1>[F:26][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[NH:17][C:18]([C:20]1([C:23](=[O:25])[NH:32][C:31]2[CH:33]=[CH:34][C:28]([F:27])=[CH:29][CH:30]=2)[CH2:22][CH2:21]1)=[O:19])[O:10][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([C:1]([NH2:2])=[O:3])[CH:9]=1

参加物

5

反応物 3

HCID 97314-FluoroanilineHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 686917891-[4-(2-Carbamoylpyridin-4-yl)oxy-2-fluorophenylaminocarbonyl]cyclopropanecarboxylic acid

生成物 1

HCID 595970164-(3-Fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridine-2-carboxamide収率 87.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 1-[4-(2-carbamoylpyridin-4-yl)oxy-2-fluorophenylaminocarbonyl]cyclopropanecarboxylic acid (743 mg) and 4-fluoroaniline (459 mg) in tetrahydrofuran (30 ml) was added 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (1.22 g), followed by stirring at room temperature for 7.5 hr. The reaction mixture was partitioned between ethyl acetate and an aqueous solution of sodium hydrogencarbonate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the resultant residue was suspended by addition of tert-butyl methyl ether—ethyl acetate (1:1, 20 ml). The solid was collected by filtration and dried under aeration to provide the titled compound as a white solid (815 mg, 87%).

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. additionthe resultant residue was suspended by addition of tert-butyl methyl ether—ethyl acetate (1:1, 20 ml)
  6. filtrationThe solid was collected by filtration
  7. customdried under aeration

出典と根拠

ORDレコード
ord-3bb6459f1797415ea579d60c36363426
出典データセット
uspto-grants-2012_10
特許番号
US08288538B2

反応ノート

読み込み中…