Hydrochloric Acid → N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

HRID 1500067노트

반응식

HRID 1500067 반응식
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]1[C:12]([C:13]([OH:15])=O)=[C:11]([C:16]([F:19])([F:18])[F:17])[C:10]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])=[N:9]1.N1C=CC=CC=1.[NH2:33][C:34]1[CH:35]=[CH:36][C:37]([Cl:43])=[C:38]([C:40](=[O:42])[CH3:41])[CH:39]=1.Cl>CN(C=O)C.ClCCl.C1COCC1>[C:40]([C:38]1[CH:39]=[C:34]([NH:33][C:13]([C:12]2[N:8]([CH3:7])[N:9]=[C:10]([C:20]([F:26])([F:25])[C:21]([F:24])([F:22])[F:23])[C:11]=2[C:16]([F:18])([F:17])[F:19])=[O:15])[CH:35]=[CH:36][C:37]=1[Cl:43])(=[O:42])[CH3:41]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 15019111-(5-amino-2-chlorophenyl)ethanoneHCID 866600921-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

생성물 1

HCID 89650518N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide수율 80%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

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온도
40 °C

실험 절차

Oxalyl chloride (0.65 ml, 0.95 g, 7.5 mmol, 1.5 eq.) followed by DMF (3 drops) were added to 1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (1.56 g, 5.00 mmol) in dichloromethane (20 ml), and the mixture was heated to 40° C. After 9 h at 40° C., the mixture was concentrated under reduced pressure, THF (20 ml) and pyridine (0.8 ml, 0.8 g, 2.0 eq.) were added, followed by 1-(5-amino-2-chlorophenyl)ethanone (0.85 g, 5.00 mmol, 1.0 eq.) in THF (5 ml). The mixture was left at room temperature for 2 d. HCl N aq. solution) was added, the mixture was extracted with ethyl acetate and the extract was washed with HCl (1N aq. solution), NaOH ON aq. solution) and sat. aq. sodium chloride solution. The extract was dried over MgSO4 and, after concentration under reduced pressure, the product was purified by column chromatography on silica gel (hexane/ethyl acetate) to give N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (1.85 g, 80%).

후처리

  1. additionwere added
  2. waitThe mixture was left at room temperature for 2 d
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe extract was washed with HCl (1N aq. solution), NaOH ON aq. solution) and sat. aq. sodium chloride solution
  5. dry with materialThe extract was dried over MgSO4
  6. concentrationafter concentration under reduced pressure
  7. customthe product was purified by column chromatography on silica gel (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-327a6421a2b54688a812cde98fc6974b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09204645B2

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