Trifluoroacetic acid → N-(2-Chloro-4-((6-cyano-7-(4-piperidylmethoxy)-4-quinolyl)oxy)phenyl)-N'-cyclopropylurea

HRID 1433555ノート

反応式

HRID 1433555 の反応式
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([CH:40]=[CH:41][C:42]=1[NH:43][C:44]([NH:46][CH:47]1[CH2:49][CH2:48]1)=[O:45])[O:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)=[C:20]([C:23]#[N:24])[CH:21]=2)[N:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O>[Cl:8][C:9]1[CH:10]=[C:11]([O:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH:27]4[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]4)=[C:20]([C:23]#[N:24])[CH:21]=3)[N:16]=[CH:15][CH:14]=2)[CH:40]=[CH:41][C:42]=1[NH:43][C:44]([NH:46][CH:47]1[CH2:49][CH2:48]1)=[O:45]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22936576Tert-butyl 4-(((4-(3-chloro-4-((cyclopropylamino)carbonyl)aminophenoxy)-6-cyano-7-quinolyl)oxy)methyl)-1-piperidinecarboxylate

生成物 1

HCID 22936852N-(2-Chloro-4-((6-cyano-7-(4-piperidylmethoxy)-4-quinolyl)oxy)phenyl)-N'-cyclopropylurea収率 99.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

After adding trifluoroacetic acid (2.5 ml) to tert-butyl 4-(((4-(3-chloro-4-((cyclopropylamino)carbonyl)aminophenoxy)-6-cyano-7-quinolyl)oxy)methyl)-1-piperidinecarboxylate (501 mg, 0.846 mmol) at room temperature, the mixture was stirred for 1 hour. The reaction solution was diluted with water (35 ml) while cooling in an ice water bath, and then sodium bicarbonate (3.5 g) was gradually added for neutralization and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was suspended in ethyl acetate and diluted with hexane, and the precipitated crystals were filtered out and blow-dried to obtain the title compound (414.4 mg, 0.842 mmol, 99.6%) as white crystals.

後処理

  1. temperaturewhile cooling in an ice water bath
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. additiondiluted with hexane
  6. filtrationthe precipitated crystals were filtered out and
  7. customblow-dried

出典と根拠

ORDレコード
ord-1e3988fe0d654e58b46c8a7a878a5e98
出典データセット
uspto-grants-2009_11
特許番号
US07612092B2

反応ノート

読み込み中…