Glycolic Acid → 3-(4-sec-butylphenyl)-2-(2-(hydroxymethyl)-1H-benzo[d]imidazol-6-yl)quinazolin-4(3H)-one

HRID 1846367Notes

Reaction equation

HRID 1846367 reaction equation
[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[C:24]([NH2:29])[CH:23]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].C([O-])(O)=O.[Na+].[C:35](O)(=O)[CH2:36][OH:37]>>[CH:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:27]=[CH:26][C:25]3[N:28]=[C:35]([CH2:36][OH:37])[NH:29][C:24]=3[CH:23]=2)=[CH:9][CH:10]=1)([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 3

HCID 757Glycolic AcidHCID 516892Sodium BicarbonateHCID 866598203-(4-sec-butylphenyl)-2-(3,4-diaminophenyl)quinazolin-4(3H)-one

Product 1

HCID 468423103-(4-sec-butylphenyl)-2-(2-(hydroxymethyl)-1H-benzo[d]imidazol-6-yl)quinazolin-4(3H)-oneYield 41%

Procedure

A solution of 3-(4-sec-butylphenyl)-2-(3,4-diaminophenyl)quinazolin-4(3H)-one (0.130 g, 0.34 mmol) was refluxed in a 70% aqueous solution of glycolic acid (10 mL) for 2 hours. The reaction was poured into a saturated solution of NaHCO3 and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 3% to 10% MeOH in CH2Cl2, afforded the title compound as a white solid (0.060 g, 41%). 1H-NMR (300 MHz, DMSO-d6): δ12.22-12.53 (m, 1H), 8.19 (d, J=7.5 Hz, 1H), 7.87-7.92 (m, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.56-7.61 (m, 2H), 7.00-7.26 (m, 6H), 5.67-5.69 (m, 1H), 4.51-4.71 (m, 2H), 1.37-1.50 (m, 2H), 1.11 (d, J=6.8 Hz, 3H), 0.58 (t, J=7.2 Hz, 3H). MS (APCI) m/z: 425 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel
  7. washeluting with 3% to 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-6e16b6dbe02f4a0ca71a0e279e8f6512
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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