Diisopropylethylamine → n-(2,4-Dioxo-6-pyrazin-2-yl-7-trifluoromethyl-1,4-dihydro-2h-quinazolin-3-yl)-methanesulfonamide

HRID 1441647Notes

Reaction equation

HRID 1441647 reaction equation
CO[C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]=1[NH2:20].ClC([O:25][C:26]1C=CC(Cl)=CC=1)=O.[CH3:33][S:34]([NH:37][NH2:38])(=[O:36])=[O:35].CCN(C(C)C)C(C)C>O1CCOCC1>[O:25]=[C:26]1[N:38]([NH:37][S:34]([CH3:33])(=[O:36])=[O:35])[C:3](=[O:21])[C:4]2[C:5](=[CH:6][C:7]([C:16]([F:17])([F:18])[F:19])=[C:8]([C:10]3[CH:15]=[N:14][CH:13]=[CH:12][N:11]=3)[CH:9]=2)[NH:20]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 269268MethanesulfonohydrazideHCID 119657822-Amino-5-pyrazin-2-yl-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 11965783n-(2,4-Dioxo-6-pyrazin-2-yl-7-trifluoromethyl-1,4-dihydro-2h-quinazolin-3-yl)-methanesulfonamideYield 76.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-5-pyrazin-2-yl-4-trifluoromethyl-benzoic acid methyl ester (235 mg, 0.79 mmol) and 4-chlorophenyl chloroformate (133 μL, 0.95 mmol) in dioxane (8 mL) was stirred at 80° C. for 105 min. After cooling to r.t., CH3SO2NHNH2 (130.6 mg, 1.19 mmol) and i-Pr2NEt (276 μL, 1.58 mmol) were added. The mixture was heated to 80° C. for 45 min, cooled to r.t., and the solvent was removed in vacuo. The residue was purified by flash chromatography (50 g silica gel, DCM→MeOH in DCM (2% to 5%)) to provide the title compound (241.5 mg, 76%) as a white powder. API-ES: m/z 402 [M+H]+, rt 2.69 min.

Workup

  1. temperatureThe mixture was heated to 80° C. for 45 min
  2. temperaturecooled to r.t.
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by flash chromatography (50 g silica gel, DCM→MeOH in DCM (2% to 5%))

Sources & evidence

ORD record
ord-ab0718161d924c0582fc1f7858197762
Source dataset
uspto-grants-2010_02
Patent number
US07655666B2

Reaction notes

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