Diisopropylethylamine → 4-Methanesulfonyl-6-{4-[2-(2-methylquinolin-5-yloxy)ethyl]piperazin-1-ylmethyl}-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 1295586ノート

反応式

HRID 1295586 の反応式
[CH3:1][S:2]([N:5]1[C:10]2[CH:11]=[C:12]([CH2:15][N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].Br[CH2:23][CH2:24][O:25][C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[CH:28]=[CH:29][C:30]([CH3:36])=[N:31]2.C(N(CC)C(C)C)(C)C>C(O)(C)C>[CH3:1][S:2]([N:5]1[C:10]2[CH:11]=[C:12]([CH2:15][N:16]3[CH2:17][CH2:18][N:19]([CH2:23][CH2:24][O:25][C:26]4[CH:35]=[CH:34][CH:33]=[C:32]5[C:27]=4[CH:28]=[CH:29][C:30]([CH3:36])=[N:31]5)[CH2:20][CH2:21]3)[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1)(=[O:4])=[O:3]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 112091394-Methanesulfonyl-6-(piperazin-1-ylmethyl)-3,4-dihydro-2H-benzo[1,4]oxazineHCID 117371925-(2-Bromoethoxy)-2-methylquinoline

生成物 1

HCID 98704464-Methanesulfonyl-6-{4-[2-(2-methylquinolin-5-yloxy)ethyl]piperazin-1-ylmethyl}-3,4-dihydro-2H-benzo[1,4]oxazine収率 36.2%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

The title compound was prepared by reaction of 4-methanesulfonyl-6-(piperazin-1-ylmethyl)-3,4-dihydro-2H-benzo[1,4]oxazine (0.145 g, 1 mmol), 5-(2-bromoethoxy)-2-methylquinoline (0.266 g, 1 mmol) and N,N-diisopropylethylamine (1.29 g, 10 mmol) in isopropyl alcohol (8 mL). The mixture was heated at reflux with stirring in a reaction block for 48 h. The reaction mixture was cooled, and the isopropyl alcohol evaporated in vacuo. The residue was partitioned between dichloromethane (5 mL), and water (5 mL). The organic layer was added onto a 10 g pre-packed silica column and eluted with 0–10% methanol in ethyl acetate. Fractions containing desired material were combined and evaporated in vacuo to give the title compound (0.180 g, 36%) as a colourless solid. Mass Spectrum (APCl+): Found 497 (MH+). C28H32N4O4S requires 496.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. temperatureThe reaction mixture was cooled
  4. customthe isopropyl alcohol evaporated in vacuo
  5. customThe residue was partitioned between dichloromethane (5 mL), and water (5 mL)
  6. additionThe organic layer was added onto a 10 g pre-packed silica column
  7. washeluted with 0–10% methanol in ethyl acetate
  8. additionFractions containing desired material
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-7ca194543f3646429c9bef934d414b4c
出典データセット
uspto-grants-2007_07
特許番号
US07244726B2

反応ノート

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