Triethylamine → HCID 44607520, 화합물

HRID 1372790

반응식

HRID 1372790 반응식
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]([OH:19])=O)=[N:9]2)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[NH2:28][C:29]1[C:34]([Cl:35])=[CH:33][C:32]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:31]([F:42])[CH:30]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.O>[Cl:35][C:34]1[C:29]([NH:28][C:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:21][CH:20]=3)[N:9]=2)=[O:19])=[CH:30][C:31]([F:42])=[C:32]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:33]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 17858807Ethyl 4-amino-5-chloro-2-fluorophenylacetateHCID 178594441-((4-methoxyphenyl)methyl)-1H-indazole-3-carboxylic acid

생성물 1

HCID 44607520HCID 44607520, 화합물수율 80%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

In methylene chloride (10 ml) was dissolved 1-(4-methoxybenzyl)-3-indazolylcarboxylic acid (630 mg, 2.23 mmol). To the resulting solution were added oxalyl chloride (292 μl, 3.53 mmol) and DMF (1 drop). The resulting mixture was stirred until the mixture became uniform. From the reaction mixture, the solvent was distilled off under reduced pressure. The residue was dissolved in methylene chloride (20 ml). Ethyl (4-amino-5-chloro-2-fluorophenyl)acetate (517 mg, 2.23 mmol) and triethylamine (621 μl, 4.46 mmol) were added to the resulting solution. The resulting mixture was heated under reflux for 15 hours. After cooling, the reaction mixture was added with water (50 ml), followed by extraction with chloroform (200 ml). The extract was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions, ethyl (5-chloro-2-fluoro-4-(1-(4-methoxybenzyl)-3-indazolylcarbonylamino)phenyl)acetate (881 mg, 80%) was obtained as a pale yellow amorphous substance.

후처리

  1. distillationFrom the reaction mixture, the solvent was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride (20 ml)
  3. temperatureThe resulting mixture was heated
  4. temperatureunder reflux for 15 hours
  5. temperatureAfter cooling
  6. extractionfollowed by extraction with chloroform (200 ml)
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions

출처 및 근거

ORD 기록
ord-64b3635a170d46b38d678f7ccc43fbfc
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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