Acetic Acid → HCID 66918821, compound

HRID 2354205Notes

Reaction equation

HRID 2354205 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([CH3:28])=[CH2:27])=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([NH:15][CH:16]2[CH2:18][CH2:17]2)=[O:14])[CH:10]=[CH:9][C:8]=1[CH3:19])=[O:5].[CH2:29](OC(OCC)OCC)C.C(O)(=O)C>C(O)C>[CH:16]1([NH:15][C:13](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([CH3:19])=[C:7]([N:6]3[C:4](=[O:5])[C:3]4[C:2](=[CH:23][CH:22]=[C:21]([O:24][CH2:25][C:26]([CH3:28])=[CH2:27])[CH:20]=4)[N:1]=[CH:29]3)[CH:12]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 66918937HCID 66918937, compound

Product 1

HCID 66918821HCID 66918821, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-amino-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-[(2-methylprop-2-en-1-yl)oxy]benzamide (3.6 g), triethylorthoformate (4.6 ml) and acetic acid (0.6 ml) in ethanol (50 ml) was heated at reflux for 18 hours. The reaction was cooled to room temperature and concentrated. The residue was partitioned between aqueous potassium carbonate solution (50 ml) and ethyl acetate (200 ml). The organic extracts were washed with brine (100 ml), dried (magnesium sulfate) and concentrated to give the crude N-cyclopropyl-4-methyl-3-[6-[(2-methylprop-2-en-1-yl)oxy]-4-oxoquinazolin-3(4H)-yl]benzamide as an oil (2.5 g) which was used directly in the next step.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated
  3. customThe residue was partitioned between aqueous potassium carbonate solution (50 ml) and ethyl acetate (200 ml)
  4. washThe organic extracts were washed with brine (100 ml)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-229eb1ccc69449daa0c13a72fe27f5c8
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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