Sodium hydride → 2-Amino-7-(4-fluoro-2-pyridin-3-yl-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(3-dimethylamino-propyl)-oxime

HRID 2046510Notes

Reaction equation

HRID 2046510 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][C:16]=3[C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:5][C:4]=2[N:3]=1.[H-].[Na+].[CH3:30][N:31]([CH3:62])[CH2:32][CH2:33][CH2:34]ON=C1CC(C2C=C(F)C=CC=2C2C=CC=CC=2)CC2N=C(N)N=C(C)C1=2>O>[CH3:30][N:31]([CH3:62])[CH2:32][CH2:33][CH2:34][O:14][N:13]=[C:8]1[CH2:7][CH:6]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH2:5][C:4]2[N:3]=[C:2]([NH2:1])[N:11]=[C:10]([CH3:12])[C:9]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75243809N-[2-amino-7-(4-fluoro-2-pyridin-3-ylphenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-ylidene]hydroxylamineHCID 866535552-amino-7-(4-fluoro-biphenyl-2-yl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(3-dimethylamino-propyl)-oxime2×

Product 1

HCID 767509082-Amino-7-(4-fluoro-2-pyridin-3-yl-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(3-dimethylamino-propyl)-oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared from 2-amino-7-(4-fluoro-2-pyridin-3-yl-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one oxime, compound 89, (100 mg, 0.275 mmol), 3-dimethyl-aminopropyl chloride hydrochloride (52 mg, 0.330 mmol) and sodium hydride (60% dispersion in oil) (35 mg, 0.881 mmol) following the same procedure used for 2-amino-7-(4-fluoro-biphenyl-2-yl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(3-dimethylamino-propyl)-oxime (compound 88) except after addition of water the solvent was removed under reduced pressure. The crude material was then extracted with ethyl acetate (20 ml), filtered and the resulting organic phase was concentrated under reduced pressure. The resulting material was washed with diethyl ether yielding the title compound.

Workup

  1. customwas removed under reduced pressure
  2. extractionThe crude material was then extracted with ethyl acetate (20 ml)
  3. filtrationfiltered
  4. concentrationthe resulting organic phase was concentrated under reduced pressure
  5. washThe resulting material was washed with diethyl ether yielding the title compound

Sources & evidence

ORD record
ord-0f3331f410cb4ffd82f77157b4e449e3
Source dataset
uspto-grants-2013_11
Patent number
US08592430B2

Reaction notes

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