1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178489836, compound

HRID 1672482Notes

Reaction equation

HRID 1672482 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([O:13][CH3:14])[C:6]([CH3:12])=[CH:7][CH:8]=2)[N:3]=1.[NH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]1.C1CCN2C(=NCCC2)CC1>CC#N>[CH3:14][O:13][C:5]1[C:6]([CH3:12])=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]1)[N:11]=[CH:10]2

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 469418452-Chloro-8-methoxy-7-methylquinazolineHCID 178511715HCID 178511715, compound

Product 1

HCID 178489836HCID 178489836, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-8-methoxy-7-methylquinazoline (20.4 g, 0.098 mol) in CH3CN (800 mL) were added trans-4-amino-cyclohexanol (22.5 g, 0.195 mol) and DBU (29.7 g, 0.195 mol) in one portion. The reaction mixture was refluxed with stirring overnight. TLC (ethyl acetate/petroleum ether=1:1) indicated the reaction was complete. The solvent was removed in vacuo. The residue was taken up with CHCl3 (550 mL), the solution was washed with water (150 mL×2). The aqueous layer was re-extracted with CHCl3 (150 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give the crude product. The crude product was re-crystallized from EtOH (130 mL)/water (200 mL) to give the title compound (17 g, 60.5%) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. customThe solvent was removed in vacuo
  3. washthe solution was washed with water (150 mL×2)
  4. extractionThe aqueous layer was re-extracted with CHCl3 (150 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customThe crude product was re-crystallized from EtOH (130 mL)/water (200 mL)

Sources & evidence

ORD record
ord-71786d32a09b40df9d265d888f143ba1
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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