Acetanthranil → 2-methyl-3-(3-(5-oxo-4,5-dihydro-1H-tetrazol-yl)phenyl)quinazolin-4(3H)-one

HRID 59048

Reaktionsgleichung

Reaktionsgleichung von HRID 59048
[CH3:1][C:2]1O[C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:13][C:14]1[CH:15]=[C:16]([N:20]2[C:24](=[O:25])[NH:23][N:22]=[N:21]2)[CH:17]=[CH:18][CH:19]=1>CC(O)=O>[CH3:1][C:2]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[C:24](=[O:25])[NH:23][N:22]=[N:21]3)[CH:15]=2)[C:4](=[O:12])[C:5]2[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:7]=1

Komponenten

4

Edukt 2

HCID 68236AcetanthranilHCID 1360622141-(3-aminophenyl)-1,4-dihydro-5H-tetrazol-5-one

Produkt 1

HCID 1371674492-methyl-3-(3-(5-oxo-4,5-dihydro-1H-tetrazol-yl)phenyl)quinazolin-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2-methyl-4H-benzo[d][1,3]oxazin-4-one (101 mg, 0.63 mmol) and 1-(3-aminophenyl)-1,4-dihydro-5H-tetrazol-5-one (111 mg, 0.63 mmol) in AcOH (10 mL) was heated to reflux and stirred overnight. Analysis indicated the formation of product. The mixture was allowed to cool and dry-loaded onto silica gel. The mixture was purified by column chromatography on silica gel using CH2Cl2/MeOH (1:0 to 9:1) as eluent to give the product (32 mg, 16% ca. 94% purity by LC/MS). The product was used directly in the next step.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureto cool and dry-loaded onto silica gel
  4. customThe mixture was purified by column chromatography on silica gel
  5. customto give the product (32 mg, 16% ca. 94% purity by LC/MS)

Quellen und Nachweise

ORD-Eintrag
ord-f0b8126e2b9f4f33b4ace88dec0c1595
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439888B2

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