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

反応式

HRID 277329 の反応式
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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

反応条件

温度
100 °C

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-5d6990ded6be4a6689857b1bd2ee51ae
出典データセット
uspto-grants-2002_03
特許番号
US06355798B1

関連ノート

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