2-methyl-2,5-dimethoxytetrahydrofurane → HCID 11965698, compound

HRID 1894075Notes

Reaction equation

HRID 1894075 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].[CH3:24][C:25]1(OC)[CH2:29][CH2:28][CH:27](OC)O1>CC(O)=O>[CH3:24][C:25]1[N:1]([CH2:2][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][C:12]=2[C:13]([F:15])([F:16])[F:14])[NH:9][C:8](=[O:17])[N:7]([NH:18][S:19]([CH3:22])(=[O:20])=[O:21])[C:6]3=[O:23])[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 109206492-methyl-2,5-dimethoxytetrahydrofuraneHCID 59164454HCID 59164454, compound

Product 1

HCID 11965698HCID 11965698, compoundYield 73%

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 (150 mg, 0.43 mmol) in conc. CH3CO2H (10 mL) was added 2-methyl-2,5-dimethoxytetrahydrofurane (62.2 mg, 0.43 mmol) and the reaction mixture was stirred for 2 h at reflux temperature. Subsequently, the solvent was evaporated and the crude light-yellow residue was recrystallized from EtOAc/cyclohexane to yield N-[6-(2-methyl-pyrrol-1-ylmethyl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (130 mg, 0.312 mmol, 73%) as a light-orange solid. 1H-NMR (DMSO-d6, 400 MHz) 3.11 ppm (s, 3H, SO2—CH3); LC-MS rt=3.994 nm; MS: m/z 416.9 [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 light-yellow residue was recrystallized from EtOAc/cyclohexane

Sources & evidence

ORD record
ord-3386292a581d4476be8d1e7236f3ab41
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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