2-Morpholinoethylamine → HCID 69659218, compound

HRID 1829061Notes

Reaction equation

HRID 1829061 reaction equation
[N:1]([CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])[O:6]1)=[C:2]=[O:3].[NH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C1COCC1>[N:27]1([CH2:26][CH2:25][NH:24][C:2]([NH:1][CH2:4][CH:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH:16][C:15]3=[O:23])[O:6]2)=[O:3])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 86590934HCID 86590934, compound

Product 1

HCID 69659218HCID 69659218, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-(3-isocyanatomethyl-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (70 mg, 0.23 mmol) and 4-(2-aminoethyl)morpholine (90.0 μl, 0.69 mmol) in THF (2.0 ml) was stirred at room temperature for 25 minutes. The reaction was heated for 5 minutes at 60° C. and then partitioned between EtOAc and water. The organic layer was washed with saturated NaHCO3 aqueous solution, and water, and then extracted with 4% HCl aqueous solution. The combined aqueous layers were basified with saturated NaHCO3 aqueous solution and extracted with EtOAc. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, and rotary evaporated to a yellow foam. The yellow foam was chromatographed through silica gel column (CHCl3 to 5% MeOH/CHCl3 gradient) to afford 1-(2-morpholin-4-yl-ethyl)-3-[3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-ylmethyl]-urea as a yellow foam (18 mg, 18%).

Workup

  1. custompartitioned between EtOAc and water
  2. washThe organic layer was washed with saturated NaHCO3 aqueous solution, and water
  3. extractionextracted with 4% HCl aqueous solution
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried with anhydrous Na2SO4
  7. customrotary evaporated to a yellow foam
  8. customThe yellow foam was chromatographed through silica gel column (CHCl3 to 5% MeOH/CHCl3 gradient)

Sources & evidence

ORD record
ord-a4f5480963d14890a2df499da7e153e3
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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