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

HRID 1295586Notes

Reaction equation

HRID 1295586 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7ca194543f3646429c9bef934d414b4c
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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