L-Methionine → HCID 136078808, compound

HRID 61638Notes

Reaction equation

HRID 61638 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[NH:7][C:6]2=[O:24].N[C@H](C(O)=O)CCSC.C([O-])(O)=O.[Na+]>CS(O)(=O)=O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[NH:7][C:6]2=[O:24]

Participants

5

Reactant 3

HCID 6137L-Methionine2×HCID 516892Sodium BicarbonateHCID 136203242HCID 136203242, compound

Product 1

HCID 136078808HCID 136078808, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 6,7-dimethoxy-2-(3-nitrophenyl)quinazolin-4(3H)-one (5.72 g, 17.5 mmol) and L-methionine (3.1 g, 20.7 mmol) in methanesulfonic acid (40 mL) was heated at 100° C. for 4.5 h. An additional aliquot of L-methionine (0.45 g, 1.36 mmol) and methanesulfonic acid (10 mL) were added and the mixture was heated for a further 2 h. The mixture was allowed to cool to RT, poured into ice water (ca. 500 mL) and was neutralized with sat. NaHCO3 solution. A solid separated out which was collected by filtration and dried under vacuum to give the desired 6-hydroxy-7-methoxy-2-(3-nitrophenyl)quinazolin-4(3H)-one. (7.3 g). HPLC retention time 5.486 min.

Workup

  1. temperaturethe mixture was heated for a further 2 h
  2. temperatureto cool to RT
  3. customA solid separated out which
  4. filtrationwas collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0b0b7658f49d4dbaab9d1d2ebc189575
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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