2,4,6-Trimethylbenzylamine → 3-(2-Amino-3-propyl-3,4-dihydro-quinazolin-6-yloxy)-N-(2,4,6-trimethyl-benzyl)-benzamide

HRID 390277Notes

Reaction equation

HRID 390277 reaction equation
[NH2:1][C:2]1[N:11]([CH2:12][CH2:13][CH3:14])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:15][C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19](Cl)=[O:20])[CH:8]=2)[N:3]=1.[CH3:25][C:26]1[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[C:27]=1[CH2:28][NH2:29]>C(Cl)Cl.O>[NH2:1][C:2]1[N:11]([CH2:12][CH2:13][CH3:14])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:15][C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]([NH:29][CH2:28][C:27]3[C:26]([CH3:25])=[CH:33][C:32]([CH3:34])=[CH:31][C:30]=3[CH3:35])=[O:20])[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 4584332,4,6-TrimethylbenzylamineHCID 586251573-(2-Amino-3-propyl-3,4-dihydro-quinazolin-6-yloxy)-benzoyl chloride

Product 1

HCID 586251303-(2-Amino-3-propyl-3,4-dihydro-quinazolin-6-yloxy)-N-(2,4,6-trimethyl-benzyl)-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(2-amino-3-propyl-3,4-dihydro-quinazolin-6-yloxy)-benzoyl chloride (0.0008 mol) in DCM (20 mL) was stirred at 0° C. and 2,4,6-trimethylbenzylamine (0.0013 mol) was added. Then TEA (q.s.) was added, and the reaction mixture was stirred at room temperature. The mixture was stirred in H2O and the organic layer was separated. The remaining layer was washed again with H2O, then the organic layer was separated, dried, and filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (gradient eluent: CH2Cl2:(CH3OH:NH3)). The purest product fractions were collected, and the solvent was evaporated. The residue was triturated under diisopropyl ether:CH3CN, and then the resulting solids were filtered off and dried to yield the title compound as a solid.

Workup

  1. additionThen TEA (q.s.) was added
  2. stirringthe reaction mixture was stirred at room temperature
  3. customthe organic layer was separated
  4. washThe remaining layer was washed again with H2O
  5. customthe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (gradient eluent: CH2Cl2:(CH3OH:NH3))
  10. customThe purest product fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was triturated under diisopropyl ether
  13. filtrationCH3CN, and then the resulting solids were filtered off
  14. customdried

Sources & evidence

ORD record
ord-9c77bc9fc40840a898c06065f20351fc
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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