2-tert-Butyl-1,3-diisopropylisourea → 4-(4-Bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid tert-butyl ester

HRID 1161814ノート

反応式

HRID 1161814 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[C:13]([Cl:15])[N:12]=[N:11][C:10]=2[C:16]([OH:18])=[O:17])=[C:4]([F:19])[CH:3]=1.[C:20](OC(=NC(C)C)NC(C)C)([CH3:23])([CH3:22])[CH3:21]>C1COCC1.C(OCC)(=O)C>[C:20]([O:17][C:16]([C:10]1[N:11]=[N:12][C:13]([Cl:15])=[CH:14][C:9]=1[NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:19])=[O:18])([CH3:23])([CH3:22])[CH3:21]

参加物

5

反応物 2

HCID 110417822-tert-Butyl-1,3-diisopropylisoureaHCID 595194954-(4-Bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid

生成物 1

HCID 595194124-(4-Bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To the stirred solution of 4-(4-bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid (516 gm, 1.49 mmol) in THF (10 ml) under argon at room temperature is added a solution of 2-tert-butyl-1,3-diisopropylisourea (1.49 g, 7.45 mmol) in THF (1.0 ml). The resulted mixture is refluxed for 6 hours. The reaction mixture is then cooled to room temperature and diluted with ethyl acetate. The organic layer is washed with 10% K2CO3 (20 ml×2) and saturated NaCl (30 ml×3), dried over Na2SO4 and concentrated in vacuum. The residue is dissolved in 30 ml of dichloromethane and the resulting white solid (urea byproduct) is filtered out. The filtrate is concentrated under reduced pressure. The residue is purified by flash column chromatography to provide the desired product.

後処理

  1. temperatureThe resulted mixture is refluxed for 6 hours
  2. washThe organic layer is washed with 10% K2CO3 (20 ml×2) and saturated NaCl (30 ml×3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuum
  5. dissolutionThe residue is dissolved in 30 ml of dichloromethane
  6. filtrationthe resulting white solid (urea byproduct) is filtered out
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customThe residue is purified by flash column chromatography

出典と根拠

ORDレコード
ord-d751dfec6de741ecbb271d61381ba469
出典データセット
uspto-grants-2010_10
特許番号
US07820664B2

反応ノート

読み込み中…