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

HRID 2046496Notes

Reaction equation

HRID 2046496 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[CH2:29][CH2:30][N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.[H-].[Na+].CN(C)CCCON=C1CC(C2C=C(F)C=CC=2C2C=CC=CC=2)CC2N=C(N)N=C(C)C1=2>>[N:31]1([CH2:30][CH2:29][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)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 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 767508882-Amino-7-biphenyl-2-yl-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(2-pyrrolidin-1-yl-ethyl)-oxime

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, (30 mg, 0.087 mmol), N-(2-chloroethyl)-pyrrolidine hydrochloride (30 mg, 0.176 mmol) and sodium hydride (60% dispersion in oil) (18 mg, 0.470 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).

Sources & evidence

ORD record
ord-6142575b0dc64149811bba0b5848298c
Source dataset
uspto-grants-2013_11
Patent number
US08592430B2

Reaction notes

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