HCID 46841135, compound → HCID 46841271, compound

HRID 1846325Notes

Reaction equation

HRID 1846325 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([NH:28]C(=O)C)=[CH:24][CH:23]=3)[C:20](=[O:32])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[CH:7][C:6]=1[CH3:33]>Cl>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([N:21]2[C:20](=[O:32])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:8]2[CH:7]=[C:6]([CH3:33])[C:5]([O:4][CH2:3][CH2:2][OH:1])=[C:10]([CH3:11])[CH:9]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 46841135HCID 46841135, compound

Product 1

HCID 46841271HCID 46841271, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(4-(2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-4-oxoquinazolin-3(4H)-yl)phenyl)acetamide (2.0 g, 4.50 mmol) in 2N HCl (50 mL) was stirred at reflux temperature for 30 minutes. Solids were filtered off and the aqueous filtrate was basified with NaOH. The filtrate was then extracted with CH2Cl2, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel eluting with 2% to 10% MeOH in CH2Cl2 afforded the title compound as an off-white solid (1.35 g, 75%). 1H-NMR (300 MHz, DMSO-d6): δ 8.14 (d, J=6.9 Hz, 1H), 7.76-7.93 (m, 1H), 7.70 (d, J=8.1 Hz, 1H), 7.45-7.64 (m, 1H), 7.03 (s, 2H), 6.85 (d, J=8.6 Hz, 2H), 6.44 (d, J=8.5 Hz, 2H), 5.21 (s, 2H), 4.84 (t, J=5.5 Hz, 1H), 3.49-3.72 (m, 4H), 2.11 (s, 6H). MS (APCI) m/z: 402 (M+H)+.

Workup

  1. temperatureat reflux temperature for 30 minutes
  2. filtrationSolids were filtered off
  3. extractionThe filtrate was then extracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel eluting with 2% to 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-195ea801497d437b8d9c341594d0933e
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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