2,5-Dimethoxytetrahydrofuran → HCID 11625241, compound

HRID 2069300Notes

Reaction equation

HRID 2069300 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].CO[CH:25]1[CH2:29][CH2:28][CH:27](OC)O1>C(O)(=O)C>[O:16]=[C:7]1[N:6]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:5](=[O:22])[C:4]2[C:9](=[CH:10][C:11]([C:12]([F:13])([F:15])[F:14])=[C:2]([N:1]3[CH:25]=[CH:29][CH:28]=[CH:27]3)[CH:3]=2)[NH:8]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 11964604N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11625241HCID 11625241, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The solution of 80 mg (0.236 mmol) ) N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide and 0.092 ml (0.709 mmol) 2,5-dimethoxy-tetrahydrofuran in 1.5 ml acetic acid is refluxed for 2 hours. After rotavapor evaporation of the solvent the residue is purified by reversed phase chromatography (C18) with an acetonitril-water gradient and the product is lyophilized to give 54 mg (59%) of N-(2,4-dioxo-6-pyrrol-1-yl-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide as a brown solid. MS (ES+): m/e =389 (M+H+).

Workup

  1. customevaporation of the solvent the residue
  2. customis purified by reversed phase chromatography (C18) with an acetonitril-water gradient

Sources & evidence

ORD record
ord-87f34c1d9ff14c9893d441d1f75c2311
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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