N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide → HCID 11640324, compound

HRID 2069310Notes

Reaction equation

HRID 2069310 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[CH:29]([CH3:30])[CH2:28][CH:27](OC)[O:26]1>C(O)(=O)C>[CH3:30][C:29]1[CH2:28][C:27](=[O:26])[N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[C:12]([F:13])([F:15])[F:14])[NH:8][C:7](=[O:16])[N:6]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:5]3=[O:22])[CH:25]=1

Participants

4

Reactant 2

HCID 11964604N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamideHCID 21444963HCID 21444963, compound

Product 1

HCID 11640324HCID 11640324, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 60 mg (0.18 mmol) of N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide in 5 ml of acetic acid are added 26 mg (0.18 mmol) of 2,5-dimethoxy-3-methyl-tetrahydro-furan (prepared according to: Markwell, Roger Edward; Hadley, Michael Stewart; Blaney, Frank Edward. Azabicycloalkane derivatives and medicaments containing them. Eur. Pat. Appl. (1983) EP 95262 A1). The reaction mixture is stirred at reflux for 10 hours. Subsequently the solvents are evaporated and the crude product is purified by flash-master chromatography (cyclohexane/ethyl acetate, from 100/0 to 20/80) to yield N-[6-(4-methyl-2-oxo-2,3-dihydro-pyrrol-1-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl] methanesulfonamide. 1H-NMR ; DMSO-d6 (400 MHz, ppm):; 8.06 (s, 1H, aromatic); 7.60 (s, 1H , aromatic); 7.13 (m, 1H, N-CH═C(CH3)); 4.24 CO—CH2-C(s, 2CO—CH2-C(CH3)); 3.16 (s, 3H, S02-CH3); 1.84 (d, 3H, CH3) [M−H]-; Agilent LC/MSD 1100 Series, LC-MS method: Column: SunFireC18, 4.6*50 mm, 3.5 μm; negative MS; water/acetonitril 95:5 to 5:95 in 5 min, flow: 1.5 ml/min.

Workup

  1. temperatureat reflux for 10 hours
  2. customSubsequently the solvents are evaporated
  3. customthe crude product is purified by flash-master chromatography (cyclohexane/ethyl acetate, from 100/0 to 20/80)

Sources & evidence

ORD record
ord-73229c7d2704438a9bcc6aad8b4fda8a
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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