Benzenebutanamine → N-[7-Nitro-2,4-dioxo-6-(4-phenyl-butylamino)-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

HRID 2069216Notes

Reaction equation

HRID 2069216 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]2=[O:21].[C:22]1([CH2:28][CH2:29][CH2:30][CH2:31][NH2:32])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[N+:12]([C:11]1[CH:10]=[C:9]2[C:4]([C:5](=[O:21])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:7](=[O:15])[NH:8]2)=[CH:3][C:2]=1[NH:32][CH2:31][CH2:30][CH2:29][CH2:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 83242BenzenebutanamineHCID 58964482N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11648022N-[7-Nitro-2,4-dioxo-6-(4-phenyl-butylamino)-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamideYield 19%

Procedure

N-(6-Fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (20 mg, 0.0628 mmol) is reacted with 4-phenyl-butylamine according to the GPA but purified, due to low solubility, by preparative TLC (eluent: hexane/ethyl acetate/acetic acid, 3/7/0.1) affording 5.4 mg (19%) of a red powder. Rt=5.93 min.

Workup

  1. custompurified, due to low solubility, by preparative TLC (eluent: hexane/ethyl acetate/acetic acid, 3/7/0.1)

Sources & evidence

ORD record
ord-1fe376790e124f8cbe917b6f21200eae
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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