Ethanol → HCID 11538207, compound

HRID 2069203Notes

Reaction equation

HRID 2069203 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].[CH:22]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23]1.C(O)C>O>[CH:22]1([NH:27][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])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 702EthanolHCID 2906CyclopentylamineHCID 58964482N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11538207HCID 11538207, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 140 mg (0.44 mmol) of N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide, 0.17 ml (1.76 mmol) of cyclopentylamine and 3 ml of ethanol is heated at 150° C. in a closed vial in a microwave reactor for 5 minutes. After cooling to room temperature, water is added and the resulting suspension is filtered. Conc. aqueous hydrochloric acid is added to the filtrate until a pH value of 2-3 is reached and the formed suspension is filtered. The residue is crystallized from ether-hexane to yield 52 mg (31%) of the title compound as red crystals, m.p. 146-155° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting suspension is filtered
  3. additionConc. aqueous hydrochloric acid is added to the filtrate until a pH value of 2-3
  4. filtrationthe formed suspension is filtered
  5. customThe residue is crystallized from ether-hexane

Sources & evidence

ORD record
ord-f8e6da89a00847ca8b4d52dd1d444c7a
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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