2,5-Dimethoxytetrahydrofuran → HCID 59164414, compound

HRID 1441594Notes

Reaction equation

HRID 1441594 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[NH:9][C:8](=[O:17])[N:7]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:6]2=[O:23].CO[CH:26]1[CH2:30][CH2:29][CH:28](OC)O1>CC(O)=O>[O:17]=[C:8]1[N:7]([NH:18][S:19]([CH3:22])(=[O:20])=[O:21])[C:6](=[O:23])[C:5]2[C:10](=[CH:11][C:12]([C:13]([F:15])([F:16])[F:14])=[C:3]([CH2:2][N:1]3[CH:26]=[CH:30][CH:29]=[CH:28]3)[CH:4]=2)[NH:9]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 59164454HCID 59164454, compound

Product 1

HCID 59164414HCID 59164414, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-(6-aminomethyl-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (100 mg, 0.28 mmol) in conc. CH3CO2H (8 mL) was added 2,5-dimethoxytetrahydrofurane (41.3 μL, 0.31 mmol) and the reaction mixture was stirred for 20 min at reflux temperature. Subsequently, the solvent was evaporated and the crude brown residue was recrystallized from EtOAc/cyclohexane to yield N-(2,4-dioxo-6-pyrrol-1-ylmethyl-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (108 mg, 0.27 mmol, 95%) as a light-brown solid. 1H-NMR (DMSO-d6, 400 MHz) 3.12 ppm (s, 3H, SO2—CH3; LC-MS rt=3.757 mn; MS: m/z 402.9 [M+H]+ Column: SunFireC18, 4.6*50 mn, 3.5 um; Positive MS Water/Acetonitrile 95:5 to 5:95 in 5 min, Flow: 1.5 mL/min

Workup

  1. temperatureat reflux temperature
  2. customSubsequently, the solvent was evaporated
  3. customthe crude brown residue was recrystallized from EtOAc/cyclohexane

Sources & evidence

ORD record
ord-ba1ef73f87394ebc86f6c06d2ea94937
Source dataset
uspto-grants-2010_02
Patent number
US07655666B2

Reaction notes

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