Acetic Acid → HCID 11487616, compound

HRID 2354225Notes

Reaction equation

HRID 2354225 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:12](OC)(OC)OC.C(O)(=O)C.[NH2:23][C:24]1[CH:25]=[C:26]([CH:33]=[CH:34][C:35]=1[CH3:36])[C:27]([NH:29][CH:30]1[CH2:32][CH2:31]1)=[O:28]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:30]1([NH:29][C:27](=[O:28])[C:26]2[CH:33]=[CH:34][C:35]([CH3:36])=[C:24]([N:23]3[C:4](=[O:6])[C:3]4[C:2](=[CH:10][CH:9]=[C:8]([I:11])[CH:7]=4)[N:1]=[CH:12]3)[CH:25]=2)[CH2:31][CH2:32]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 119838543-amino-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 11487616HCID 11487616, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 2-amino-5-iodobenzoic acid (1.0 g), trimethyl orthoformate (0.83 ml), and acetic acid (0.022 ml) in toluene (15 ml) was heated under reflux for 2 hours. 3-Amino-N-cyclopropyl-4-methylbenzamide (0.65 g) was added to the reaction mixture and stirred at reflux for 16 hours. The reaction mixture was allowed to cool and diluted with ethyl acetate. The organic solution was then washed with 1N HCl solution, 2N NaOH solution (x 2), brine, dried (magnesium sulfate), and concentrated to give N-cyclopropyl-3-(6-iodo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzamide (AZ12233711) (1.22 g) as an off white solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.70 (m, 2H), 2.14 (s, 3H), 2.85 (m, 1H), 7.52 (d, 1H), 7.58 (d, 1H), 7.88 (s, 1H), 7.92 (d, 1H), 8.20 (d, 1H), 8.34 (s, 1H), 8.42 (d, 1H), 8.49 (s, 1H); Mass Spectrum: M+H+ 446.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureat reflux for 16 hours
  4. temperatureto cool
  5. washThe organic solution was then washed with 1N HCl solution, 2N NaOH solution (x 2), brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-34df34549e3a411faff7e73d34716dc8
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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