1,2-Dichloroethane → HCID 178429228, 화합물

HRID 734686노트

반응식

HRID 734686 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])[NH:15][C:14]([CH3:19])=[C:13]1[C:20]([OH:22])=O.[NH2:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][N:28]=[C:27]2[Br:33].C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Br:33][C:27]1[C:26]2[C:30](=[CH:31][CH:32]=[C:24]([NH:23][C:20]([C:13]3[CH:12]([C:3]4[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=4[F:1])[CH2:17][C:16](=[O:18])[NH:15][C:14]=3[CH3:19])=[O:22])[CH:25]=2)[NH:29][N:28]=1

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 688271204-[2-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 178507356HCID 178507356, 화합물

생성물 1

HCID 178429228HCID 178429228, 화합물수율 20.2%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

The product of Example 21, Step 2 (200 mg, 0.63 mmol, 1.00 equiv), 5-amino-3-bromoindazole (134 mg, 0.63 mmol, 1.0 equiv), and EDC (145 mg, 0.757 mmol, 1.20 equiv) were suspended in 1.75 mL DMF. Et3N (0.106 mL, 0.757 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) and further purified by reverse-phase HPLC (10-80% CH3CN/H2O—NH4OH to pH 10 over 17 minutes, retention time 12.59 min) to provide 65 mg (20%) of the title compound as a white solid. MS (ES+) m/e 511 [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)
  7. customfurther purified by reverse-phase HPLC (10-80% CH3CN/H2O—NH4OH to pH 10 over 17 minutes, retention time 12.59 min)

출처 및 근거

ORD 기록
ord-935e756d862e4a668359b95d80b91848
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592357B2

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