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

HRID 1846367노트

반응식

HRID 1846367 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-6e16b6dbe02f4a0ca71a0e279e8f6512
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952021B2

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