Triethylamine → 6-bromo-1-oxo-4-phenyl-2-(4-[1,2,3]thiadiazole-4-ylbenzyl)-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750320ノート

反応式

HRID 750320 の反応式
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7](=O)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4].[S:23]1[CH:27]=[C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=2)[N:25]=[N:24]1.C(N(CC)CC)C>CO>[CH3:1][O:2][C:3]([C:5]1[N:33]([CH2:32][C:31]2[CH:30]=[CH:29][C:28]([C:26]3[N:25]=[N:24][S:23][CH:27]=3)=[CH:35][CH:34]=2)[C:7](=[O:6])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27372881-[4-(1,2,3-Thiadiazol-4-Yl)phenyl]methanamineHCID 66990710Methyl 6-bromo-1-oxo-4-phenyl-1H-isochromene-3-carboxylate

生成物 1

HCID 691560326-bromo-1-oxo-4-phenyl-2-(4-[1,2,3]thiadiazole-4-ylbenzyl)-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester収率 15%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 6-bromo-1-oxo-4-phenyl-1H-isochromen-3-carboxylic acid methyl ester (359 mg) in methanol (20 ml) were added 4-[1,2,3]thiadiazol-4-ylbenzylamine (956 mg) and triethylamine (1.4 ml) and the mixture was stirred at room temperature for 72 hrs. The solvent was evaporated under reduced pressure, and the residue was partitioned between 1N hydrochloric acid and ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure, 4N hydrochloric acid ethyl acetate solution (5 ml) was added to the obtained residue, and the mixture was stirred at room temperature for 10 hrs. The solvent was evaporated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogen carbonate solution and saturated brine and dried by adding sodium sulfate. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1→1/1) to give the title compound (80 mg, 15%).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between 1N hydrochloric acid and ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. customdried
  5. additionby adding sodium sulfate
  6. customThe solvent was evaporated under reduced pressure, 4N hydrochloric acid ethyl acetate solution (5 ml)
  7. additionwas added to the obtained residue
  8. stirringthe mixture was stirred at room temperature for 10 hrs
  9. customThe solvent was evaporated under reduced pressure, water
  10. additionwas added
  11. extractionthe mixture was extracted with ethyl acetate
  12. washThe extract was washed with saturated sodium hydrogen carbonate solution and saturated brine
  13. customdried
  14. additionby adding sodium sulfate
  15. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1→1/1)

出典と根拠

ORDレコード
ord-372ac2800f16404aafe621f82eba7a99
出典データセット
uspto-grants-2008_07
特許番号
US07402595B2

反応ノート

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