4-Hydroxypyrrolidine → N-[6-(3-Hydroxy-pyrrolidin-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

HRID 2069225Notes

Reaction equation

HRID 2069225 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].[NH:22]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]1>>[OH:27][CH:24]1[CH2:25][CH2:26][N:22]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[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]3=[O:21])[CH2:23]1

Participants

3

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 58964482N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11545484N-[6-(3-Hydroxy-pyrrolidin-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamideYield 58%

Procedure

N-(6-Fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (30 mg, 0.0943 mmol) is reacted with pyrrolidin-3-ol according to the GPA affording 21 mg (58%) of a red powder. Rt=4.22 min.

Sources & evidence

ORD record
ord-9defc8a90e8649a390341e1d83ad0e8d
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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