Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde → HCID 11538926, compound

HRID 2069301Notes

Reaction equation

HRID 2069301 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[NH:8][C:7](=[O:16])[N:6]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:5]2=[O:22].C[O:24][CH:25]1[CH:29]([CH:30]=O)[CH2:28][CH:27](OC)O1>C(O)(=O)C>[CH:25]([C:29]1[CH:28]=[CH:27][N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[C:12]([F:13])([F:15])[F:14])[NH:8][C:7](=[O:16])[N:6]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:5]3=[O:22])[CH:30]=1)=[O:24]

Participants

4

Reactant 2

HCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 11964604N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11538926HCID 11538926, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 100 mg (0.296 mmol) of N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide in 2 ml acetic acid is added a solution of 2,5-dimethoxy-tetrahydrofuran-3-carbaldehyde in 1 ml acetic acid and the mixture is refluxed for 3 hours. The solvent is removed by rotavapor evaporation and the brown oil is purified by reversed phase chromatography (C18) with an acetonitril-water gradient to give 80 mg (65%) of N-[6-(3-formyl-pyrrol-1-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide as a black solid. MS (ES+): m/e =417 (M+H+).

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. customThe solvent is removed by rotavapor evaporation
  3. customthe brown oil is purified by reversed phase chromatography (C18) with an acetonitril-water gradient

Sources & evidence

ORD record
ord-1e2fa05b507b41cca1fce2eced5d9b8a
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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