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

HRID 734705
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HRID 734705 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([OH:18])=O)=[C:4]([F:19])[CH:3]=1.[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][C:26]([F:31])=[C:27]([NH2:30])[CH:28]=2)[NH:23][N:22]=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][C:26]([F:31])=[C:27]([NH:30][C:16]([C:9]3[CH:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=4[F:19])[CH2:13][C:12](=[O:14])[NH:11][C:10]=3[CH3:15])=[O:18])[CH:28]=2)[NH:23][N:22]=1
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참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 688260574-(4-Chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 1785072033-chloro-6-fluoro-1H-indazol-5-amine

생성물 1

HCID 178429202N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-4-(4-chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide수율 7%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

The product of Example 3 Step 2 (191 mg, 0.668 mmol, 1.00 equiv), the product of Step 2 (125 mg, 0.668 mmol, 1.0 equiv), and EDC (153 mg, 0.802 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.112 mL, 0.802 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 reverse-phase HPLC (20-90% CH3CN/H2O—NH4OH to pH 10 over 13 minutes, retention time 7.79 min) to provide 20 mg (7%) of the title compound as a white solid. MS (ES+) m/e 452 [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 reverse-phase HPLC (20-90% CH3CN/H2O—NH4OH to pH 10 over 13 minutes, retention time 7.79 min)

출처 및 근거

ORD 기록
ord-8d585ffb8f87406eb6d71dbecbadcc4d
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592357B2

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