Ethylmorpholine → HCID 58031814, compound

HRID 240262Notes

Reaction equation

HRID 240262 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]#[C:16][CH3:17])[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:48][C:49]1[CH:50]=[CH:51][C:52]([CH3:61])=[C:53]([CH:60]=1)[O:54][CH:55]([CH3:59])[C:56](O)=[O:57]>CN(C=O)C.[Cl-].[Na+]>[Br:48][C:49]1[CH:50]=[CH:51][C:52]([CH3:61])=[C:53]([CH:60]=1)[O:54][CH:55]([CH3:59])[C:56]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]#[C:16][CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1)=[O:57]

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66628683HCID 66628683, compoundHCID 66628746HCID 66628746, compound

Product 1

HCID 58031814HCID 58031814, compound

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 150 mg (0.56 mmol) of ethyl 3-(4-aminophenyl)hex-4-ynoate, 193 mg (1.68 mmol) of N-ethylmorpholine, 103 mg (0.67 mmol) of HOBt hydrate and 104 mg (0.67 mmol) of EDAC in 3 ml of DMF was added to a solution of 160 mg (0.62 mmol) of 2-(5-bromo-2-methylphenoxy)propionic acid in 2 ml of DMF. After 3 days 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 ethyl 3-{4-[2-(5-bromo-2-methylphenoxy)propionylamino]phenyl}hex-4-ynoate.

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-c2e43067d6a64d1d91d3613308822a8c
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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