Ethylmorpholine → HCID 178499407, compound

HRID 1490094Notes

Reaction equation

HRID 1490094 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10](NC(N)=N)[C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1CCC([N:24]=[C:25]=[N:26]C2CCCCC2)CC1.C1C=CC2N(O)N=[N:39]C=2C=1.Cl.[NH2:44][CH2:45][CH2:46][N:47]1[CH2:51][C:50](=[O:52])[N:49]([CH:53]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:54]([O:56][CH3:57])=[O:55])[C:48]1=[O:64].C(N1CCOCC1)C>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([NH:44][CH2:45][CH2:46][N:47]2[CH2:51][C:50](=[O:52])[N:49]([CH:53]([C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)[C:54]([O:56][CH3:57])=[O:55])[C:48]2=[O:64])=[O:13])=[C:8]([NH:24][C:25]([NH2:26])=[NH:39])[CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 86751451HCID 86751451, compoundHCID 178513023HCID 178513023, compound

Product 1

HCID 178499407HCID 178499407, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

270 mg (1.13 mmol) of 4-nitroguanidinophenylacetic acid are dissolved in 50 ml of dimethylformamide, and 270 mg (1.25 mmol) of DCC and 150 mg (1.13 mmol) of HOBt are then added at 0° C. The mixture is stirred for 30 minutes and 370 mg (1.13 mmol) of methyl (3-(2-aminoethyl)-2,5-dioxoimidazolidin-1-yl)phenylacetate hydrochloride and 150 μl (1.13 mmol) of N-ethylmorpholine are then added. After stirring at room temperature for 20 h, the mixture is concentrated and ethyl acetate and methanol are added to the residue and the insoluble dicyclohexylurea is filtered off with suction. The filtrate is concentrated and methylene chloride is then added, and the solution is washed with sodium hydrogen carbonate solution and potassium hydrogen sulphate solution, dried and concentrated.

Workup

  1. stirringAfter stirring at room temperature for 20 h
  2. concentrationthe mixture is concentrated
  3. additionethyl acetate and methanol are added to the residue
  4. filtrationthe insoluble dicyclohexylurea is filtered off with suction
  5. concentrationThe filtrate is concentrated
  6. additionmethylene chloride is then added
  7. washthe solution is washed with sodium hydrogen carbonate solution and potassium hydrogen sulphate solution
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1c8660cabf664403af32fee9b0fb2840
Source dataset
uspto-grants-1997_10
Patent number
US05681838

Reaction notes

Loading…