Dimethylformamide → 7-(difluoromethoxy)-N-((6-phenyl-[1,2,4]-triazolo[4,3-b]pyridazin-3-yl)methyl)-1,5-naphthyridin-4-amine

HRID 219153

반응식

HRID 219153 반응식
CN(C=O)C.[C:6]1([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([CH2:21][NH:22][C:23]4[CH:24]=[CH:25][N:26]=[C:27]5[C:32]=4[N:31]=[CH:30][C:29]([OH:33])=[CH:28]5)=[N:19][N:20]=3)[N:17]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:35]([F:40])([F:39])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>O>[F:39][CH:35]([F:40])[O:33][C:29]1[CH:28]=[C:27]2[C:32]([C:23]([NH:22][CH2:21][C:18]3[N:16]4[N:17]=[C:12]([C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=5)[CH:13]=[CH:14][C:15]4=[N:20][N:19]=3)=[CH:24][CH:25]=[N:26]2)=[N:31][CH:30]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 1359874788-((6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylamino)-1,5-naphthyridin-3-ol

생성물 1

HCID 576913497-(difluoromethoxy)-N-((6-phenyl-[1,2,4]-triazolo[4,3-b]pyridazin-3-yl)methyl)-1,5-naphthyridin-4-amine수율 17.7%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

DMF (0.5 mL) and water (0.1 mL) were added to a pressure vessel containing 8-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylamino)-1,5-naphthyridin-3-ol (50 mg, 135 μmol), sodium 2-chloro-2,2-difluoroacetate (47 mg, 311 μmol), cesium carbonate (62 mg, 190 μmol). The reaction mixture was stirred at 100° C. for 18 h, cooled to RT and concentrated in vacuo. Purification by MPLC (DCM/MeOH+1% NH4OH: 100/0 to 90/10) afforded the title compound (10 mg, 17% yield). MS m/z=420.1 [M+H]+. Calc'd for C21H15F2N7O: 419.40.

후처리

  1. temperaturecooled to RT
  2. concentrationconcentrated in vacuo
  3. customPurification by MPLC (DCM/MeOH+1% NH4OH: 100/0 to 90/10)

출처 및 근거

ORD 기록
ord-07c3e49acd4a4b2ebfb3ba18d2df86b6
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198448B2

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