Acetic Acid → HCID 135622210, compound

HRID 1884006Notes

Reaction equation

HRID 1884006 reaction equation
[O:1]=[C:2]1[C:11]2[C:10]3[CH:12]=[C:13]([C:16]#[C:17][Si](C)(C)C)[CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]=[C:4]([NH:22]C(=O)C(C)(C)C)[NH:3]1.C([O-])([O-])=O.[K+].[K+].C(O)(=O)C>CO.O>[NH2:22][C:4]1[NH:3][C:2](=[O:1])[C:11]2[C:10]3[CH:12]=[C:13]([C:16]#[CH:17])[CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 135838202HCID 135838202, compound

Product 1

HCID 135622210HCID 135622210, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of N-(1,2-dihydro-1-oxo-9-(trimethylsilylethynyl)benzo[f]quinazolin-3-yl)pivalamide (0.24 g, 0.61 mmol) and K2CO3 (0.50 g, 3.6 mmol) in methanol (˜50 ml) was stirred at reflux for 2.5 hours. The solution was then diluted with water (˜20 ml) acidified with acetic acid, and the resulting solid filtered and dried at 90° C. under reduced pressure. The solid was resuspended in ethanol (˜20 ml), filtered, and dried to give 3-amino-9-ethynyl benzo[f]quinazolin-1(2H)-one (0.084 g) as a tan solid. 1H NMR (DMSO-d, 200 MHz) δ: 4.26 (s, 1H, ethynylCH), 6.63 (br s, 2H, NH2), 7.32 (d, J=9 Hz, 1H, Ar), 7.47 (dd, J=8, 2 Hz, 1H, Ar), 7.87 (d, J=8 Hz, 1H, Ar), 8.02 (d, J=9 Hz, 1H, Ar), 9.78 (s, 1H, Ar), 11.34 (br s, 1H, NH). Mass spectrum (CI-CH4): 236 (M+1, 100%). Anal. Calculated for C14H9N3O: C, 71.48; H, 3.86; N, 17.86. Found: C, 71.30; H, 3.92; N, 17.68.

Workup

  1. temperatureat reflux for 2.5 hours
  2. filtrationthe resulting solid filtered
  3. customdried at 90° C. under reduced pressure
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-afdb176dcbaa4246a958feace3a6956f
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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