Triethylamine → 2-Amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(2-dimethylamino-ethyl)-oxime

HRID 2046467Notes

Reaction equation

HRID 2046467 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[C:8](=[N:13][OH:14])[CH2:7][CH:6]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH2:5][C:4]=2[N:3]=1.[H-].[Na+].Cl.[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28]Cl.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][O:14][N:13]=[C:8]1[CH2:7][CH:6]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH2:5][C:4]2[N:3]=[C:2]([NH2:1])[N:11]=[C:10]([CH3:12])[C:9]1=2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 866535532-amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one oxime2×

Product 1

HCID 866535522-Amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(2-dimethylamino-ethyl)-oxime

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one oxime, compound 30, (109 mg, 0.38 mmol) in DMF (2 ml) under nitrogen was added sodium hydride (60% dispersion in oil) (18 mg, 0.44 mmol) and the mixture was stirred at ambient temperature for 10 min. 2-Dimethylaminoethylchloride hydrochloride (54 mg, 0.38 mmol) and triethylamine (52 μl, 0.38 mmol) were added to the reaction mixture, which was stirred and heated at 80° C. until complete disappearance of 2-amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one oxime was observed by LC-MS. Ethyl acetate (5 ml) was added to the mixture and the solution was washed three times with water (3×5 ml). The organic phase was dried with MgSO4, filtered and the solvent removed under reduced pressure to furnish the title compound as a brown solid.

Workup

  1. stirringwas stirred
  2. washthe solution was washed three times with water (3×5 ml)
  3. dry with materialThe organic phase was dried with MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-224baa7a94a74acda2012f07cba9e21c
Source dataset
uspto-grants-2013_11
Patent number
US08592430B2

Reaction notes

Loading…