Serinol → HCID 11696760, compound

HRID 2069194Notes

Reaction equation

HRID 2069194 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].[NH2:22][CH:23]([CH2:26][OH:27])[CH2:24][OH:25]>>[OH:25][CH2:24][CH:23]([NH:22][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])[CH2:26][OH:27]

Participants

3

Reactant 2

HCID 68294SerinolHCID 58964482N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11696760HCID 11696760, compoundYield 28.6%

Conditions

Temperature
150 °C

Procedure

A mixture of 100 mg (0.314 mmol) of N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide and 142 mg (1.55 mmol) of 2-amino-1,3-propanediol in a closed vial is heated in a microwave reactor at 150° C. for 20 minutes. After cooling, the reaction mixture is concentrated to dryness and the product purified by HPLC-chromatography on a RP-C18 column using a gradient of water/acetonitril/0.1% TFA as eluent. 35 mg of the title compound are obtained as a red powder, m.p. 126-145° C. (decomp.).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated to dryness
  3. customthe product purified by HPLC-chromatography on a RP-C18 column

Sources & evidence

ORD record
ord-f745f29587d4406990bf4766493624ef
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

Loading…