Dichloromethane → HCID 67187943, compound

HRID 545635Notes

Reaction equation

HRID 545635 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[C:20]([CH:27]=[CH:28]C=3C)[C:21]([NH:23][CH:24]3[CH2:26][CH2:25]3)=[O:22])=[CH:15][CH:16]=2)[CH2:11][NH:10][C:9]1=[O:31].[C:32](C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[CH2:46]([Cl:48])Cl>>[CH:24]1([NH:23][C:21](=[O:22])[C:20]2[CH:27]=[CH:28][C:46]([Cl:48])=[C:18]([C:14]3[CH:13]=[C:12]4[C:17](=[CH:16][CH:15]=3)[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:32])[C:9](=[O:31])[N:10]=[CH:11]4)[CH:19]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 24966725HCID 24966725, compound

Product 1

HCID 67187943HCID 67187943, compound

Procedure

To a stirred solution of 3-(1-(2-chlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-6-yl)-N-cyclopropyl-4-methylbenzamide (0.1233 g, 285 μmol) in DCM was added DDQ (71 mg, 314 μmol) and the resulting dark-colored mixture was stirred at RT for 3 h. The reaction was quenched with NaHCO3(aq) and water (10 mL each) and the separated aqueous layer was extracted with 5% MeOH in DCM (3×6 mL). The combined organic layers were washed with, 1N NaOH(aq), brine, dried (Na2SO4), and concentrated to give the crude residue. Flash column chromatographic purification (5% MeOH in DCM) of the crude residue followed by washing the concentrated pure product fractions with ethyl acetate provided N-cyclopropyl-4-chloro-3-(2-oxo-1-o-tolyl-1,2-dihydroquinazolin-6-yl)benzamide as a white solid. MS m/e 430 (M+H)+.

Workup

  1. customThe reaction was quenched with NaHCO3(aq) and water (10 mL each)
  2. extractionthe separated aqueous layer was extracted with 5% MeOH in DCM (3×6 mL)
  3. washThe combined organic layers were washed with, 1N NaOH(aq), brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give the crude residue
  7. customFlash column chromatographic purification (5% MeOH in DCM) of the crude residue
  8. washby washing the concentrated pure product fractions with ethyl acetate

Sources & evidence

ORD record
ord-6dd583304fb64bc48a963351370ea200
Source dataset
uspto-grants-2011_05
Patent number
US07935709B2

Reaction notes

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