Acetic Anhydride → N-(4-(5,5-dimethyl-4-oxo-3-(4-(quinolin-2-ylmethoxy)phenyl)-4,5-dihydrofuran-2-yl)phenyl)acetamide

HRID 655477Notes

Reaction equation

HRID 655477 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10](=[O:15])[C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.[CH3:34][C:35](OC(C)=O)=[O:36]>C(Cl)Cl.O>[CH3:14][C:11]1([CH3:13])[O:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:35](=[O:36])[CH3:34])=[CH:3][CH:4]=2)=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[CH:18][CH:17]=2)[C:10]1=[O:15]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 59354866HCID 59354866, compound

Product 1

HCID 59354836N-(4-(5,5-dimethyl-4-oxo-3-(4-(quinolin-2-ylmethoxy)phenyl)-4,5-dihydrofuran-2-yl)phenyl)acetamideYield 26.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(4-aminophenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one (0.07 g, 0.16 mmol) in DCM (5 mL) were added Ac2O (0.018 mL, 0.19 mmol) and TEA (0.04 mL, 0.32 mmol) at 0° C. under N2 atmosphere. The reaction mixture was stirred at RT for 14 h. The reaction mixture was diluted with water and extracted with DCM (2×15 mL). Combined organic layers were washed with water (2×5 mL), brine and dried over anhydrous Na2SO4. After filtration and evaporation, the crude material was purified by silica gel column chromatography to afford N-(4-(5,5-dimethyl-4-oxo-3-(4-(quinolin-2-ylmethoxy)phenyl)-4,5-dihydrofuran-2-yl) phenyl)acetamide (20 mg, 26%), as an off white solid. 1H NMR (500 MHz, CDCl3): δ 8.22 (d, J=8.5 Hz, 1H), 8.08 (d, J=7.9 Hz, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.74 (t, J=8.2 Hz, 1H), 7.68 (d, J=8.2 Hz, 1H), 7.64 (d, J=8.2 Hz, 2H), 7.56 (t, J=8.5 Hz, 1H), 7.48 (d, J=7.4 Hz, 2H), 7.22 (d, J=7.5 Hz, 2H), 7.08 (d, J=8.9 Hz, 2H), 5.42 (s, 2H), 2.22 (s, 3H), 1.58 (s, 6H). MS: [M+Na]: m/z=501.3, [M+H]: m/z=479.3. HPLC: 95.9% (RT-2.32 min), Column: Acquity BEH-C-18, 50×2.1 mm, 1.7 um. Mobile Phase: 0.025% TFA in Water (A), ACN (B), Flow rate: 0.5 ml/min (Gradient).

Workup

  1. extractionextracted with DCM (2×15 mL)
  2. washCombined organic layers were washed with water (2×5 mL), brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration and evaporation
  5. customthe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-63512c763a544f96ae3f0e02fcc1cf80
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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