4-Chloro-2-phenylquinazoline → [1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-(2-phenyl-quinazolin-4-yl)-amine

HRID 2242956Notes

Reaction equation

HRID 2242956 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1)[CH3:19]>CC(N(C)C)=O>[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[CH2:24][N:25]1[CH2:26][CH2:27][CH:28]([NH:31][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:3]=2)[CH2:29][CH2:30]1)[CH3:19]

Participants

4

Reactant 2

HCID 809774-Chloro-2-phenylquinazolineHCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×

Product 1

HCID 67147321[1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-(2-phenyl-quinazolin-4-yl)-amineYield 3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-chloro-2-phenyl-quinazoline (36.1 mg, 0.15 mmol, 1.0 equiv; commercially available) and 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (47.6 mg, 0.18 mmol, 1.2 equiv; intermediate A1) in DMAc (1.5 mL) was heated by microwave irradiation to 180° C. for 10 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 1.6 mg (3%) of the title compound. MS (ISP): 469.4 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-adece709ee6e4015ad35a19f006bf163
Source dataset
uspto-grants-2010_03
Patent number
US07674804B2

Reaction notes

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