2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 67188551, compound

HRID 545636Notes

Reaction equation

HRID 545636 reaction equation
COC1C=CC(C[N:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:18]4[CH:19]=[C:20]([CH:28]=[CH:29][C:30]=4[CH3:31])[C:21]([N:23]([CH:25]4[CH2:27][CH2:26]4)[CH3:24])=[O:22])[CH:15]=3)[N:10]([CH3:32])[C:9]2=[O:33])=CC=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(O)(C(F)(F)F)=O>[CH:25]1([N:23]([CH3:24])[C:21](=[O:22])[C:20]2[CH:28]=[CH:29][C:30]([CH3:31])=[C:18]([C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[N:10]([CH3:32])[C:9](=[O:33])[N:8]=[CH:17]4)[CH:19]=2)[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 67188280HCID 67188280, compound

Product 1

HCID 67188551HCID 67188551, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-(3-(4-methoxybenzyl)-1-methyl-2-oxo-1,2,3,4-tetrahydroquinazolin-6-yl)-N-cyclopropyl-N,4-dimethylbenzamide (0.445 g, 948 μmol) in TFA(4.00 ml) in a microwave reaction vessel was sealed and heated at 100° C. for 20 min under microwave irradiation. After cooling, the mixture was filtered through a short path of Celite and the filter cake was washed with EtOAc (3×10 mL). The mixture was concentrated and the crude product was taken up to a solution of DCM (5.00 ml), treated with DDQ (215 mg, 948 μmol) at 0° C. for 10 min then stirred at RT for 1 h. The reaction was quenched with NaHCO3(aq) and water (10 mL each) and the separated aqueous layer was extracted with DCM (5 mL×3). The combined organic phases were washed with 1N NaOH(aq), brine, dried (Na2SO4), and concentrated to give a crude residue. Flash column chromatographic purification (5% MeOH in DCM) of the residue provided the title compound N-cyclopropyl-N,4-dimethyl-3-(1-methyl-2-oxo-1,2-dihydroquinazolin-6-yl)benzamide as a pale tan solid. MS m/e 308 (M+H)+.

Workup

  1. customwas sealed
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through a short path of Celite
  4. washthe filter cake was washed with EtOAc (3×10 mL)
  5. concentrationThe mixture was concentrated
  6. customThe reaction was quenched with NaHCO3(aq) and water (10 mL each)
  7. extractionthe separated aqueous layer was extracted with DCM (5 mL×3)
  8. washThe combined organic phases were washed with 1N NaOH(aq), brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customto give a crude residue
  12. customFlash column chromatographic purification (5% MeOH in DCM) of the residue

Sources & evidence

ORD record
ord-05fb9d96ca84481783d331c9ce668e3c
Source dataset
uspto-grants-2011_05
Patent number
US07935709B2

Reaction notes

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