2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-1H-indole

HRID 512837노트

반응식

HRID 512837 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[N:19][C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)=[CH:21][CH:22]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.CCOC(C)=O>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[N:19][C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)=[CH:21][CH:22]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 715715696-Fluoro-1-[1-[6-(1-methylpyrazol-4-yl)pyridazin-3-yl]piperidin-4-yl]-2,3-dihydroindole

생성물 1

HCID 715852956-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-1H-indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)indoline (75 mg, 0.2 mmol) in THF (3 mL) was added DDQ (54 mg, 0.24 mmol). The resulting mixture was stirred at room temperature for 30 min and was poured into EtOAc (30 mL). The organic layer washed with Na2CO3(aq) (30 mL), H2O (30 mL), dried (Na2SO4), and filtered. The solvent was removed and the resulting residue purified by column using 80-90-100% EtOAc/(CH2Cl2/hexane=1/1) as the eluent to yield 6-fluoro-1-(1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-yl)-1H-indole, which was then converted to its corresponding HCl salt.

후처리

  1. washThe organic layer washed with Na2CO3(aq) (30 mL), H2O (30 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe solvent was removed
  5. customthe resulting residue purified by column

출처 및 근거

ORD 기록
ord-66a671102de949ac93c5c54a2924daed
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102669B2

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