2-Morpholinoethylamine → HCID 67315123, compound

HRID 1011401Notes

Reaction equation

HRID 1011401 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:11]1[N:16]=[CH:15][C:14]2[C:17](=[C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][C:23]3=[O:31])[O:18][CH:19]([CH2:20][CH3:21])[C:13]=2[C:12]=1Cl>O1CCOCC1>[CH2:20]([CH:19]1[C:13]2[CH:12]=[C:11]([NH:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:16]=[CH:15][C:14]=2[C:17](=[C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][C:23]2=[O:31])[O:18]1)[CH3:21]

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 76798897HCID 76798897, compound

Product 1

HCID 67315123HCID 67315123, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-morpholin-4-yl-ethylamine (320 mg, 2.46 mmol) in 3 mL of dioxane is treated with 3-(6,7-Dichloro-1-ethyl-1H-furo[3,4-c]pyridin-3-ylidene)-1,3-dihydro-indol-2-one (100 mg, 0.32 mmol) in one portion and the reaction mixture is heated at 100° C. until no starting material remains. The reaction mixture is cooled to room temperature and concentrated. The residue is purified by chromatography (silica gel, 5% MeOH-EtOAc) to give the title compound as a solid (36 mg, 28%).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue is purified by chromatography (silica gel, 5% MeOH-EtOAc)

Sources & evidence

ORD record
ord-9500bd0023614838b6b744842dca6407
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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