Acetic Acid → HCID 68810009, compound

HRID 2354215Notes

Reaction equation

HRID 2354215 reaction equation
N[C:2]1[CH:10]=[CH:9][C:8](OC)=CC=1C(O)=O.COC(OC)OC.C(O)(=O)C.N[C:25]1[CH:26]=[C:27]([CH:35]=[CH:36][C:37]=1C)[C:28]([NH:30]C1(C)CC1)=[O:29]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:8][C:9]1([C:26]2[CH:25]=[CH:37][CH:36]=[CH:35][C:27]=2[C:28]([NH2:30])=[O:29])[CH2:2][CH2:10]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 2779305-Methoxyanthranilic acidHCID 66918926HCID 66918926, compound

Product 1

HCID 68810009HCID 68810009, compoundYield 114.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 2-amino-5-methoxybenzoic acid (4 g), trimethylorthoformate (3.93 ml), and acetic acid (0.137 ml) in toluene (100 ml) was heated under reflux for 2 hours. 3-amino-4-methyl-N-(1-methylcyclopropyl)benzamide (4.39 g) was added to the reaction mixture and stirring continued in refluxing toluene for 16 hours. The reaction mixture was allowed to cool and then was diluted with ethyl acetate. The organic solution was then washed with 1N HCl solution, 2N NaOH solution (×2), brine, dried (magnesium sulfate) and concentrated to a cream coloured solid. The solid was dissolved in ethyl acetate and the insoluble material removed by filtration. Iso-hexane was added to the filtrate and concentrated to give 3-(6-methoxy-4-oxoquinazolin-3(4H)-yl)-4-methyl-N-(1-methylcyclopropylbenzamide (4.3 g); NMR Spectrum: (DMSOd6) 0.59 (m, 2H), 0.72 (m, 2H), 1.35 (s, 3H), 2.12 (s, 3H), 3.89 (s, 3H), 7.50 (m, 2H), 7.56 (m, 1H), 7.72 (d, 1H), 7.83 (s, 1H), 7.88 (d, 1H), 8.17 (s, 1H), 8.63 (s, 1H); Mass Spectrum: M+Na+ 486.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. washThe organic solution was then washed with 1N HCl solution, 2N NaOH solution (×2), brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated to a cream
  7. dissolutionThe solid was dissolved in ethyl acetate
  8. customthe insoluble material removed by filtration
  9. additionIso-hexane was added to the filtrate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ea7707419189428f95c7b66b8d3e1c7c
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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