Diisopropylethylamine → 6-[4-[4-(Diphenylmethoxy)piperidino]butylamino][1,2,4]triazolo[1,5-b]pyridazine

HRID 1169026ノート

反応式

HRID 1169026 の反応式
[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:27]1[CH:28]=[CH:29][C:30]2[N:31]([N:33]=[CH:34][N:35]=2)[N:32]=1.C(N(C(C)C)C(C)C)C>C(O)CCC>[C:20]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:27]3[CH:28]=[CH:29][C:30]4[N:31]([N:33]=[CH:34][N:35]=4)[N:32]=3)[CH2:11][CH2:10]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 112406116-Chloro-(1,2,4)triazolo(1,5-b)pyridazineHCID 117392591-Piperidinebutanamine, 4-(diphenylmethoxy)-

生成物 1

HCID 110049766-[4-[4-(Diphenylmethoxy)piperidino]butylamino][1,2,4]triazolo[1,5-b]pyridazine収率 9.1%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

4-(Diphenylmethoxy)-1-piperidinebutanamine (1.83 g) and 6-chloro[1,2,4]triazolo[1,5-b]pyridazine (557 mg) were dissolved in 1-butanol (30 ml), followed by addition of N-ethyldiisopropylamine (931 mg). The mixture was refluxed under heating for 14 hours. After being cooled, the mixture was concentrated under reduced pressure, followed by addition of ice-water and extraction with ethyl acetate. The extract was washed with an aqueous sodium chloride saturated solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with a mixture of ethyl acetate, methanol and triethylamine (45:5:1). Fractions containing the objective compound were collected and concentrated. The resulting crystals were collected, washed with ethyl ether and dried to yield the title compound (149 mg).

後処理

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 14 hours
  3. temperatureAfter being cooled
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionfollowed by addition of ice-water and extraction with ethyl acetate
  6. washThe extract was washed with an aqueous sodium chloride saturated solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washeluted with a mixture of ethyl acetate, methanol and triethylamine (45:5:1)
  10. additionFractions containing the objective compound
  11. customwere collected
  12. concentrationconcentrated
  13. customThe resulting crystals were collected
  14. washwashed with ethyl ether
  15. customdried

出典と根拠

ORDレコード
ord-a821833f505a4bc7b26d508fd2daf261
出典データセット
uspto-grants-2003_09
特許番号
US06627630B1

反応ノート

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