1,4-Dioxane → 3-(3-{2-[(2-methoxy-ethyl)-propyl-amino]-ethyl}-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one

HRID 1829055Notes

Reaction equation

HRID 1829055 reaction equation
[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]([CH2:20]COS(C)(=O)=O)[O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH3:27][O:28][CH2:29][CH2:30][NH:31][CH2:32][CH2:33][CH3:34].O1CCOC[CH2:36]1>>[CH3:27][O:28][CH2:29][CH2:30][N:31]([CH2:32][CH2:33][CH3:34])[CH2:36][CH2:20][CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]2=[O:1])[O:12]1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 12238049N-(2-Methoxyethyl)propylamineHCID 72382355Methanesulfonic Acid 2-[3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-ethyl Ester

Product 1

HCID 696591763-(3-{2-[(2-methoxy-ethyl)-propyl-amino]-ethyl}-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one

Procedure

A solution of methanesulfonic acid 2-[3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-ethyl ester (50 mg, 0.135 mmol) and N-(2-methoxyethyl)-N-propylamine (191 μl, 1.35 mmol) in dioxane (0.8 ml) was heated at 75° C. for 19 hours. The reaction was partitioned between EtOAc and water. The EtOAc layer was washed with water, brine, dried with anhydrous Na2SO4 and rotary evaporated to give brown oil. The brown oil was chromatographed with CHCl3 to give 3-(3-{2-[(2-methoxy-ethyl)-propyl-amino]-ethyl}-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one as a yellow-brown film (11 mg, 20%).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. washThe EtOAc layer was washed with water, brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customrotary evaporated
  5. customto give brown oil
  6. customThe brown oil was chromatographed with CHCl3

Sources & evidence

ORD record
ord-2c21ac4ddf1c4737b29c302951920111
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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