Ethyl Acetate → HCID 69300072, compound

HRID 2218129Notes

Reaction equation

HRID 2218129 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=3)[C:14]2=[O:26])=[CH:8][CH:7]=1.ClC(Cl)(O[C:32](=[O:38])OC(Cl)(Cl)Cl)Cl.[NH:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:42][CH2:41]1.C(OCC)(=O)C>O1CCCC1>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][N:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:20]=[CH:21][C:22]([NH:25][C:32]([N:40]4[C:48]5[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=5)[CH2:42][CH2:41]4)=[O:38])=[CH:23][CH:24]=3)[C:14]2=[O:26])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10328IndolineHCID 94429TriphosgeneHCID 69299466HCID 69299466, compound

Product 1

HCID 69300072HCID 69300072, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 3-{4-[3-(4-aminophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}propionic acid methyl ester in tetrahydrofuran (5 mL) was added to a stirred solution of triphosgene (0.135 g, 0.45 mmol) in tetrahydrofuran (5 mL) at 0° C. After 2 hours a solution of indoline (0.054 g, 0.45 mmol) in tetrahydrofuran (2.5 mL) was added and stirring continued at room temperature for 18 hours. The mixture was then poured into ethyl acetate (25 mL) and washed sequentially with hydrochloric acid (10 mL, 1M), saturated aqueous sodium bicarbonate (10 mL) and brine before drying over anhydrous magnesium sulfate. After filtration and evaporation to dryness the residue was chromatographed on silica gel with a gradient of 1:1 rising to 3:1 ethyl acetate to hexane to give the title compound as a solid.

Workup

  1. washwashed sequentially with hydrochloric acid (10 mL, 1M), saturated aqueous sodium bicarbonate (10 mL) and brine
  2. dry with materialbefore drying over anhydrous magnesium sulfate
  3. filtrationAfter filtration and evaporation to dryness the residue
  4. customwas chromatographed on silica gel with a gradient of 1:1 rising to 3:1 ethyl acetate to hexane

Sources & evidence

ORD record
ord-30ffba2fbb454b5dbf88cd8092ce9e83
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

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