Sodium Hydroxide → N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]cyclopropanecarboxamide

HRID 42257노트

반응식

HRID 42257 반응식
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([NH2:25])[C:13]4[C:17]([CH:18]=3)=[N:16][N:15](C3CCCCO3)[CH:14]=4)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCN(C(C)C)C(C)C.[CH:35]1([C:38](Cl)=[O:39])[CH2:37][CH2:36]1.[OH-].[Na+]>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][NH:16]4)=[C:12]([NH:25][C:38]([CH:35]4[CH2:37][CH2:36]4)=[O:39])[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

생성물 1

HCID 44540492N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]cyclopropanecarboxamide수율 20.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (46 mg, 0.137 mmol) in DCM (1 ml) was added DIPEA (0.119 ml, 0.684 mmol) and cyclopropyl carbonyl chloride (29 mg, 0.274 mmol). The reaction was stirred at room temperature for 1 hour, then 2M sodium hydroxide solution (2 ml) was added and the reaction stirred at room temperature for a further 1 hour. The organic layer was collected by passing through a hydrophobic frit. The aqueous layer was washed several times with DCM. The organic extracts were combined and solvent removed by blow down. The residue was dissolved in methanol (2 ml) and 4M HCl in 1,4-dioxane added (2 ml). The reaction was stirred at room temperature for 1 hour. The solvent was removed by blow down and the residue purified by mass directed preparative HPLC (method B). The residue was freeze dried to give the title compound as a pale brown solid (9 mg).

후처리

  1. stirringthe reaction stirred at room temperature for a further 1 hour
  2. customThe organic layer was collected
  3. washThe aqueous layer was washed several times with DCM
  4. customsolvent removed by blow down
  5. dissolutionThe residue was dissolved in methanol (2 ml)
  6. addition4M HCl in 1,4-dioxane added (2 ml)
  7. stirringThe reaction was stirred at room temperature for 1 hour
  8. customThe solvent was removed by blow down
  9. customthe residue purified by mass
  10. customdried

출처 및 근거

ORD 기록
ord-5fb2b92beda1432980417bf5d066420a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536169B2

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