N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide → HCID 58964505, compound

HRID 2069308Notes

Reaction equation

HRID 2069308 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]([CH2:30][O:31][CH:32]2[CH2:37]CCC[O:33]2)[CH2:28][CH:27](OC)O1>C(O)(=O)C>[CH3:21][S:18]([NH:17][N:6]1[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:27]=[CH:28][C:29]([CH2:30][O:31][C:32](=[O:33])[CH3:37])=[CH:25]3)[CH:3]=2)[NH:8][C:7]1=[O:16])(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 11964604N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamideHCID 69338490HCID 69338490, compound

Product 1

HCID 58964505HCID 58964505, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 130 mg (0.39 mmol) of N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide in 5 ml of acetic acid a solution of 95 mg (0.39 mmol) of 2-(2,5-dimethoxy-tetrahydro-furan-3-ylmethoxy)-tetrahydro-pyran (prepared according to Frydman, Benjamin; Ojea, Maria I. 1,4-Diaminobutanes from furans: a new synthetic approach to substituted putrescines. Tetrahedron Letters (1998), 39(27), 4765-4768) is added and the reaction mixture is stirred at reflux for 3 hours. The solvent is evaporated at HV overnight to yield acetic acid 1-(3-methanesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-yl)-1H-pyrrol-3-ylmethyl ester. 1H-NMR ; DMSO-d6 (400 MHz, ppm): 7.85 (s, 1H , aromatic); 7.62 (s, 1H , aromatic); 7.03 (s, 1H, N-CH═C(CH2) in pyrrol); 6.91 (m, 1H, N-CH═CH in pyrrol); 6.27 (m, 1H, CH═CH-C(CH2)-N in pyrrol); 4.96 (s, 2H, CH2-OCOCH3); 3.16 (s, 3H, SO2-CH3); 2.03 (s, 3H, CH2-OCOCH3); LC-MS: 459 [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. additionTetrahedron Letters (1998), 39(27), 4765-4768) is added
  2. temperatureat reflux for 3 hours
  3. customThe solvent is evaporated at HV overnight

Sources & evidence

ORD record
ord-9e7e6cbf870148989454eed33304cbb4
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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