2-methyl-2,5-dimethoxytetrahydrofurane → HCID 58964523, compound

HRID 2069306Notes

Reaction equation

HRID 2069306 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].[CH3:23][C:24]1(OC)[CH2:28][CH2:27][CH:26](OC)O1>C(O)(=O)C>[CH3:23][C:24]1[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:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 109206492-methyl-2,5-dimethoxytetrahydrofuraneHCID 11964604N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 58964523HCID 58964523, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 200 mg (0.59 mmol) of N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide in 10 ml of acetic acid, 87 mg (0.60 mmol) of 2-methyl-2,5-dimethoxy-tetrahydrofuran is added and the reaction mixture is stirred at reflux for 5 hours. Subsequently the solvent is evaporated and the residue is dried for I day at 60° C. and high vacuum to yield N-[6-(2-methyl-pyrrol-1-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide. 1H-NMR; DMSO-d6 (400 MHz, ppm): 7.69 (s, 1H, aromatic); 7.54 (s, 1H , aromatic); 6.6 (s, 1H, N-CH═CH in pyrrol); 5.97 (t, 1H, CH═CH═CH in pyrrol); 5.83 (m, 1H, CH═CH-C(CH3)-N in pyrrol); 3.05 (s, 3H, SO2-CH3); 1.82 (s, 3H, pyrrol-1-CH3). LC-MS: 403 [M+H]+; Agilent LC/MSD 1100 Series; LC-MS method: Column: SunFireC18, 4.6*50 mm, 3.5 μm; positive MS; water/acetonitril 95:5 to 5:95 in 5 min, flow: 1.5 ml/min.

Workup

  1. temperatureat reflux for 5 hours
  2. customSubsequently the solvent is evaporated
  3. customthe residue is dried for I day at 60° C.

Sources & evidence

ORD record
ord-45102b9197be49ba85f110a75117d824
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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