Sodium hydride → 2-Amino-7-biphenyl-2-yl-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(3-piperazin-1-yl-propyl)-oxime

HRID 2046500Notes

Reaction equation

HRID 2046500 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][CH:18]=[CH:17][C:16]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:5][C:4]=2[N:3]=1.Cl.Cl.Cl[CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.[H-].[Na+].CN(C)CCCON=C1CC(C2C=C(F)C=CC=2C2C=CC=CC=2)CC2N=C(N)N=C(C)C1=2>O>[N:33]1([CH2:32][CH2:31][CH2:30][O:14][N:13]=[C:8]2[CH2:7][CH:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:5][C:4]3[N:3]=[C:2]([NH2:1])[N:11]=[C:10]([CH3:12])[C:9]2=3)[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 447849821-(3-Chloropropyl)piperazine dihydrochlorideHCID 767508942-amino-7-biphenyl-2-yl-4-methyl-7,8-dihydro-6H-quinazolin-5-one oximeHCID 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 767509042-Amino-7-biphenyl-2-yl-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(3-piperazin-1-yl-propyl)-oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared from 2-amino-7-biphenyl-2-yl-4-methyl-7,8-dihydro-6H-quinazolin-5-one oxime, compound 66, (100 mg, 0.290 mmol), 1-(3-chloro-propyl)-piperazine dihydrochloride (82 mg, 0.350 mmol) and sodium hydride (60% dispersion in oil) (18 mg, 465 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 taken up in methanol (20 ml) and the resulting solution was filtered. The solvent was removed under reduced pressure. The title compound was purified by preparative HPLC (UV directed fraction collection).

Workup

  1. customwas removed under reduced pressure
  2. filtrationthe resulting solution was filtered
  3. customThe solvent was removed under reduced pressure
  4. customThe title compound was purified by preparative HPLC (UV directed fraction collection)

Sources & evidence

ORD record
ord-80774948088642e3bdc3c0153908c570
Source dataset
uspto-grants-2013_11
Patent number
US08592430B2

Reaction notes

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