6-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine → N-(7-Cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)-N-(1-methyl-1H-1,2,4-triazol-3-ylmethyl)amine

HRID 277329

반응식

HRID 277329 반응식
Cl[C:2]1[C:3]([CH:17]2[CH2:20][CH2:19][CH2:18]2)=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:10]=2)[N:7]=1.Cl.[CH3:22][N:23]1[CH:27]=[N:26][C:25]([CH2:28][NH2:29])=[N:24]1>C(N(CC)CC)C.CN(C=O)C>[CH:17]1([C:3]2[C:2]([NH:29][CH2:28][C:25]3[N:26]=[CH:27][N:23]([CH3:22])[N:24]=3)=[N:7][N:6]3[C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:9][N:10]=[C:5]3[CH:4]=2)[CH2:20][CH2:19][CH2:18]1

참가 물질

5

반응물 2

HCID 110005936-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazineHCID 18314526(1-methyl-1H-1,2,4-triazol-3-yl)methanamine hydrochloride

생성물 1

HCID 9841820N-(7-Cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)-N-(1-methyl-1H-1,2,4-triazol-3-ylmethyl)amine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

반응 조건

온도
100 °C

실험 절차

A mixture of 6-chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine (144 mg, 0.52 mmol) and C-(1-methyl-1H-1,2,4-triazol-3-yl)methylamine hydrochloride (300 mg, 2.0 mmol) in triethylamine (1 ml) and dry DMF (1 ml) was stirred and heated at 100° C. in a sealed tube for 20 hours. Upon cooling the volatiles were removed in vacuo, and the residue was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. The aqueous was further extracted with dichloromethane (x2). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatograhy on silica gel, eluting with 2%→5%→10% methanol-dichloromethane to give, in order of elution:

후처리

  1. temperatureUpon cooling the volatiles
  2. customwere removed in vacuo
  3. customthe residue was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate
  4. extractionThe aqueous was further extracted with dichloromethane (x2)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatograhy on silica gel
  9. washeluting with 2%→5%→10% methanol-dichloromethane
  10. customto give, in order of elution

출처 및 근거

ORD 기록
ord-5d6990ded6be4a6689857b1bd2ee51ae
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355798B1

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