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

HRID 734681
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HRID 734681 반응식
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17](O)=[O:18])=[CH:5][CH:4]=1.[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][C:31]=1[F:32])[NH:28][N:27]=[CH:26]2.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[F:32][C:31]1[CH:30]=[C:29]2[C:25]([CH:26]=[N:27][NH:28]2)=[CH:24][C:23]=1[NH:22][C:17]([C:10]1[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:21])([F:20])[F:1])=[CH:8][CH:7]=2)[CH2:14][C:13](=[O:15])[NH:12][C:11]=1[CH3:16])=[O:18]
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참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 160998632-Methyl-6-oxo-4-(4-(trifluoromethyl)phenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acidHCID 450905046-fluoro-1H-indazol-5-amine

생성물 1

HCID 113738464-(4-(trifluoromethyl)phenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide수율 22.4%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

The product of Example 5, Step 2 (200 mg, 0.67 mmol, 1.00 equiv), 5-amino-6-fluoroindazole (101 mg, 0.67 mmol, 1.0 equiv), and EDC (153 mg, 0.80 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.112 mL, 0.80 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 (20-100% EtOAc in Hexanes) to provide 65 mg (22%) of the title compound as an off white solid. MS (ES+) m/e 433 [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 (20-100% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-df542294df854277afd387230fd386b9
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592357B2

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