Ethyl ether methylene chloride → 2-(2-Hydroxy-ethylcarbamoyloxymethyl)-5,7-dimethyl-3-(2-methylsulfamoylphenyl)-4-oxo-3,4-dihydro-quinazoline-6-carboxylic Acid Propyl Ester

HRID 1039368Notes

Reaction equation

HRID 1039368 reaction equation
[OH:1][CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19](=[O:23])(=[O:22])[NH:20][CH3:21])[C:11](=[O:24])[C:10]2[C:5](=[CH:6][C:7]([CH3:29])=[C:8]([C:26]([OH:28])=[O:27])[C:9]=2[CH3:25])[N:4]=1.C(OC(C1C(C)=C2C(=CC=1C)N=[C:40]([CH2:46][O:47]CC1C=CC=CC=1)[N:39](C1C=CC=CC=1S(=O)(=O)NC)[C:38]2=[O:66])=O)C.C(O[CH2:71][CH3:72])C.Cl[CH2:74]Cl>Br>[CH2:74]([O:27][C:26]([C:8]1[C:9]([CH3:25])=[C:10]2[C:5](=[CH:6][C:7]=1[CH3:29])[N:4]=[C:3]([CH2:2][O:1][C:38](=[O:66])[NH:39][CH2:40][CH2:46][OH:47])[N:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](=[O:22])(=[O:23])[NH:20][CH3:21])[C:11]2=[O:24])=[O:28])[CH2:71][CH3:72]

Participants

5

Reactant 3

HCID 21881112Ethyl ether methylene chlorideHCID 66815225HCID 66815225, compoundHCID 668153472-Hydroxymethyl-5,7-dimethyl-3-(2-methylsulfamoylphenyl)-4-oxo-3,4-dihydro-quinazoline-6-carboxylic acid

Product 1

HCID 115775242-(2-Hydroxy-ethylcarbamoyloxymethyl)-5,7-dimethyl-3-(2-methylsulfamoylphenyl)-4-oxo-3,4-dihydro-quinazoline-6-carboxylic Acid Propyl Ester

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
80 °C

Procedure

2-Hydroxymethyl-5,7-dimethyl-3-(2-methylsulfamoylphenyl)-4-oxo-3,4-dihydro-quinazoline-6-carboxylic acid: 2-Benzyloxymethyl-5,7-dimethyl-3-(2-methylsulfamoyl-phenyl)-4-oxo-3,4-dihydro-quinazoline-6-carboxylic acid ethyl ester (3 g, 5.6 mmol) is dissolved in 47% hydrobromic acid. The reaction mixture is stirred at 80° C. overnight, then at 90° C. for 5 h, then at 95° C. for a further 5 h. The reaction mixture is evaporated in vacuo to give a brown solid, which is suspended in diethyl ether/dichloromethane and stirred overnight. Filtration, followed by washing with dichloromethane then ether and drying in vacuo provides the title compound as a sandy brown solid.

Workup

  1. waitat 90° C. for 5 h
  2. waitat 95° C. for a further 5 h
  3. customThe reaction mixture is evaporated in vacuo
  4. customto give a brown solid, which
  5. stirringstirred overnight
  6. filtrationFiltration
  7. washby washing with dichloromethane
  8. dry with materialether and drying in vacuo

Sources & evidence

ORD record
ord-1841e4003ee84ffb82996d022c352ac4
Source dataset
uspto-grants-2013_10
Patent number
US08552015B2

Reaction notes

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