Sodium Hydroxide → 3-[3-[[2-[3-(2,2-Dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]carbamoyl]phenyl]prop-2-enoic acid

HRID 539805ノート

反応式

HRID 539805 の反応式
C([O:3][C:4](=[O:39])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:38])[NH:14][C:15]2[CH:20]=[CH:19][C:18]3=[N:21][C:22]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[CH:25]=4)=[CH:23][N:17]3[N:16]=2)[CH:8]=1)C.[OH-].[Na+]>C1COCC1.CO>[CH3:34][C:33]([CH3:36])([CH3:35])[C:32]([NH:31][C:26]1[CH:25]=[C:24]([C:22]2[N:21]=[C:18]3[N:17]([CH:23]=2)[N:16]=[C:15]([NH:14][C:13]([C:9]2[CH:8]=[C:7]([CH:6]=[CH:5][C:4]([OH:39])=[O:3])[CH:12]=[CH:11][CH:10]=2)=[O:38])[CH:20]=[CH:19]3)[CH:29]=[CH:28][C:27]=1[CH3:30])=[O:37]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 67983260Ethyl-3-[3-[[2-[3-(2,2-dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]carbamoyl]phenyl]prop-2-enoate

生成物 1

HCID 680891733-[3-[[2-[3-(2,2-Dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]carbamoyl]phenyl]prop-2-enoic acid収率 62.8%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A 20-mL vial is charged with ethyl-3-[3-[[2-[3-(2,2-dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]carbamoyl]phenyl]prop-2-enoate (0.042 g, 0.08 mmol) and a solution of THF-MeOH (1 mL, 1:1). To this mixture is added aqueous NaOH (1 mL, 1 M), then stirred at 50° C. for 1 hour. The mixture is concentrated to remove the organics and extracted with EtOAc once. Aqueous HCl (1M) is added to lower the pH to 2 and the resulting solids are filtered to give the title compound (0.025 g), which is used without further purification. LCMS (m/z)=498.5 [M+H]+, tR=2.47 min.

後処理

  1. concentrationThe mixture is concentrated
  2. customto remove the organics and
  3. extractionextracted with EtOAc once
  4. additionAqueous HCl (1M) is added
  5. filtrationthe resulting solids are filtered

出典と根拠

ORDレコード
ord-d010a2e2766649c184dce2e6e7f1dfb5
出典データセット
uspto-grants-2014_10
特許番号
US08871767B2

反応ノート

読み込み中…