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1,2-Dichloroethane → N-(6-Fluoro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl)phenyl]-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734710
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HRID 734710 반응식
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][C:16](=[O:18])[N:15]([CH3:19])[C:14]([CH3:20])=[C:13]1[C:21]([OH:23])=O.[NH2:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][C:33]=1[F:34])[NH:30][N:29]=[CH:28]2.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[F:34][C:33]1[CH:32]=[C:31]2[C:27]([CH:28]=[N:29][NH:30]2)=[CH:26][C:25]=1[NH:24][C:21]([C:13]1[CH:12]([C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=2[F:1])[CH2:17][C:16](=[O:18])[N:15]([CH3:19])[C:14]=1[CH3:20])=[O:23]
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참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 450905046-fluoro-1H-indazol-5-amineHCID 690027054-[2-Fluoro-4-(trifluoromethyl)phenyl]-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

생성물 1

HCID 11476792N-(6-Fluoro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoromethyl)phenyl]-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide수율 3%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

The product of Step 2 (165 mg, 0.498 mmol, 1.00 equiv), 5-amino-6-fluoroindazole (75 mg, 0.498 mmol, 1.0 equiv), and EDC (114 mg, 0.598 mmol, 1.20 equiv) were suspended in 1.0 mL DMF. Et3N (0.083 mL, 0.598 mmol, 1.2 equiv) was added and the solution was stirred at room temperature for 18 hrs. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (0-80% EtOAc in Hexanes) and further purified by reverse-phase HPLC (10-80% CH3CN/H2O, 0.1% TFA over 24 minutes, retention time 15.55 min) to provide 7 mg (3%) of the title compound as a white solid. MS (ES+) m/e 465 [M+H]+

후처리

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated en vacuo
  6. customThe residue was purified by flash chromatography (0-80% EtOAc in Hexanes)
  7. customfurther purified by reverse-phase HPLC (10-80% CH3CN/H2O, 0.1% TFA over 24 minutes, retention time 15.55 min)

출처 및 근거

ORD 기록
ord-1274fa04b68d49da83c90d3ada33d50d
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592357B2

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