Ethylmorpholine → HCID 58031793, compound

HRID 240263Notes

Reaction equation

HRID 240263 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:15][CH3:16])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(N1CCOCC1)C.C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.[Br:47][C:48]1[CH:59]=[C:58]([CH:60]([CH3:62])[CH3:61])[CH:57]=[CH:56][C:49]=1[O:50][CH:51]([CH3:55])[C:52](O)=[O:53]>CN(C=O)C.[Cl-].[Na+]>[Br:47][C:48]1[CH:59]=[C:58]([CH:60]([CH3:62])[CH3:61])[CH:57]=[CH:56][C:49]=1[O:50][CH:51]([CH3:55])[C:52]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:15][CH3:16])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1)=[O:53]

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22687730HCID 22687730, compoundHCID 66628645HCID 66628645, compound

Product 1

HCID 58031793HCID 58031793, compound

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 150 mg (0.67 mmol) of ethyl 3-(4-aminophenyl)-3-methoxypropionate, 116 mg (1.01 mmol) of N-ethylmorpholine, 123 mg (0.81 mmol) of HOBt hydrate and 125 mg (0.81 mmol) of EDAC in 2 ml of DMF was added a solution of 212 mg (0.74 mmol) of 2-(2-bromo-4-isopropylphenoxy)propionic acid in 2 ml of DMF. After 22 h at room temperature, the reaction mixture was diluted with sodium chloride solution and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. This gave 331 mg of ethyl 3-{4-[2-(2-bromo-4-isopropylphenoxy)propionylamino]phenyl}-3-methoxypropionate.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e560ead1b2ec4630be5c60b5bcd48823
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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