Dimethylformamide → HCID 58778670、化合物

HRID 1372742

反応式

HRID 1372742 の反応式
[CH3:1][N:2]1[C:10]([C:11]([OH:13])=O)=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8]2)=[N:3]1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[NH2:25][C:26]1[C:31]([Cl:32])=[CH:30][C:29]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:28]([F:39])[CH:27]=1.C(N(CC)CC)C>C1C=CC=CC=1>[Cl:32][C:31]1[C:26]([NH:25][C:11]([C:10]2[N:2]([CH3:1])[N:3]=[C:4]3[C:9]=2[CH:8]=[CH:7][CH:6]=[CH:5]3)=[O:13])=[CH:27][C:28]([F:39])=[C:29]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:30]=1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 70605372-Methyl-2H-indazole-3-carboxylic acidHCID 17858807Ethyl 4-amino-5-chloro-2-fluorophenylacetate

生成物 1

HCID 58778670HCID 58778670、化合物収率 27.1%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

To 2-methylindazole-3-carboxylic acid (650 mg, 3.69 mmol) and DMF (29.0 μl, 0.37 mmol) was added benzene (20 ml). Under stirring at room temperature, oxalyl chloride (0.39 ml, 4.43 mmol) was added dropwise to the resulting mixture. After completion of the dropwise addition, the reaction mixture was stirred for further 1 hour at room temperature. A solution of ethyl (4-amino-5-chloro-2-fluorophenyl)acetate (855 mg, 3.69 mmol) and triethylamine (3.09 ml, 22.1 mmol) in benzene (3.0 ml), which had been prepared in advance, was added dropwise to the reaction mixture, and the mixture was heated under reflux for 16 hours. The reaction mixture was then cooled to room temperature, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (5:1, v/v) eluate fractions, ethyl (5-chloro-2-fluoro-4-((2-methyl-3-indazolylcarbonyl)amino)phenyl)acetate (390 mg, 27%) was obtained as a pale yellow solid.

後処理

  1. additionAfter completion of the dropwise addition
  2. stirringthe reaction mixture was stirred for further 1 hour at room temperature
  3. additionwas added dropwise to the reaction mixture
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 16 hours
  6. temperatureThe reaction mixture was then cooled to room temperature
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationdistilled under reduced pressure
  11. customto remove the solvent
  12. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (5:1

出典と根拠

ORDレコード
ord-0870bf82d9e24a0cb22dfac5df9e4d52
出典データセット
uspto-grants-2007_01
特許番号
US07157487B2

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