2,5-Dimethoxytetrahydrofuran → HCID 59164414, compound

HRID 1894074Notes

Reaction equation

HRID 1894074 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 nm; MS: m/z 402.9 [M+H]+Column: SunFireC18, 4.6*50 nm, 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-e53992bd8cd64517a0846d96325f8e88
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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