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

HRID 734754노트

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HRID 734754 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[NH2:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][C:23](=[O:25])[NH:22][C:21]([CH3:26])=[C:20]2[C:27](O)=[O:28])=[CH:15][C:14]=1[O:30][CH3:31].C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][C:23](=[O:25])[NH:22][C:21]([CH3:26])=[C:20]2[C:27]([NH:11][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][C:2]=2[F:1])[NH:8][N:7]=[CH:6]3)=[O:28])=[CH:15][C:14]=1[O:30][CH3:31]

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 450905046-fluoro-1H-indazol-5-amineHCID 688272564-[4-Chloro-3-(methyloxy)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

생성물 1

HCID 578452824-[4-Chloro-3-(methyloxy)phenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide수율 29.3%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
30 °C

실험 절차

6-Fluoro-1H-indazol-5-amine (102 mg, 0.676 mmol, 1.0 equiv) was combined with the product of Example 93, Step 4 (0.200 g, 0.676 mmol, 1.0 equiv), EDC (155 mg, 0.812 mmol, 1.2 equiv) and Et3N (113 μL, 0.812 mmol, 1.2 equiv) in DMF (2 mL) and stirred at 30° C. for 18 hours. 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. Solid precipitated out of the organic phase and was filtered and triturated with ether to provide 85.0 mg (29%) of the title compound as a white solid. MS (ES+) m/e 429 [M+H]+

후처리

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. customSolid precipitated out of the organic phase
  4. filtrationwas filtered
  5. customtriturated with ether

출처 및 근거

ORD 기록
ord-fde6ac4e9b4c4a2996f12cdabf9324cc
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592357B2

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