Sodium hydride → HCID 76750928, compound

HRID 2046501Notes

Reaction equation

HRID 2046501 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[CH2:28][CH2:29][CH2:30][CH2:31][C:32]#[CH:33].[H-].[Na+].CN(C)CCCON=C1CC(C2C=C(F)C=CC=2C2C=CC=CC=2)CC2N=C(N)N=C(C)C1=2>O>[CH2:33]([O:14][N:13]=[C:8]1[CH2:7][CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:5][C:4]2[N:3]=[C:2]([NH2:1])[N:11]=[C:10]([CH3:12])[C:9]1=2)[CH2:32][CH2:31][CH2:30][C:29]#[CH:28]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2720016-Chloro-1-hexyneHCID 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 76750928HCID 76750928, compound

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, (50 mg, 0.145 mmol), 6-chloro-1-hexyne (21 μl, 0.174 mmol) and sodium hydride (60% dispersion in oil) (11 mg, 0.465 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 (mass 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 (mass directed fraction collection)

Sources & evidence

ORD record
ord-7bccfa4cdeb44e92af0ecb641cf58ad7
Source dataset
uspto-grants-2013_11
Patent number
US08592430B2

Reaction notes

Loading…