Isopropyl iodide → (5''-[1-(1-Isopropyl-piperidin-4-yl)-1H-pyrazol-4-yl]-[2,2';4',3'']terpyridin-6'-yl)-methyl-amine

HRID 1798537노트

반응식

HRID 1798537 반응식
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[C:5]([C:15]2[CH:16]=[N:17][CH:18]=[C:19]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH:25]=3)[CH:20]=2)[CH:4]=1.I[CH:33]([CH3:35])[CH3:34]>CN(C=O)C.CCOC(C)=O>[CH:33]([N:29]1[CH2:30][CH2:31][CH:26]([N:24]2[CH:25]=[C:21]([C:19]3[CH:20]=[C:15]([C:5]4[CH:4]=[C:3]([NH:2][CH3:1])[N:8]=[C:7]([C:9]5[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=5)[CH:6]=4)[CH:16]=[N:17][CH:18]=3)[CH:22]=[N:23]2)[CH2:27][CH2:28]1)([CH3:35])[CH3:34]

참가 물질

5

반응물 2

HCID 6362Isopropyl iodideHCID 68757252Methyl-[5''-(1-piperidin-4-yl-1H-pyrazol-4-yl)-[2,2';4',3'']terpyridin-6'-yl]-amine

생성물 1

HCID 86633647(5''-[1-(1-Isopropyl-piperidin-4-yl)-1H-pyrazol-4-yl]-[2,2';4',3'']terpyridin-6'-yl)-methyl-amine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of Methyl-[5″-(1-piperidin-4-yl-1H-pyrazol-4-yl)-[2,2′;4′,3″]terpyridin-6′-yl]-amine (Example 2.183) (1 eq, 0.122 mmol, 50 mg) in DMF (3 ml) cooled at 0° C. is added 2-iodopropane (7 eq, 0.854 mmol, 0.084 ml) and the reaction is stirred at room temperature for 5 hours. The reaction mixture is dissolved in EtOAc and washed with water. The combined organic extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is purified by reverse phase column chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA). The appropriate fractions by HPLC are combined and concentrated in vacuo. The resulting residue is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 454.

후처리

  1. washwashed with water
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by reverse phase column chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA)
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting residue is dissolved in MeOH
  8. washeluting with MeOH
  9. concentrationconcentrated in vacuo
  10. customdried under vacuum

출처 및 근거

ORD 기록
ord-2d491bfb3f004783bf378ec3c8ac9865
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343966B2

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