Diethyl {[(4-iodophenyl)carbonyl]amino}propandioate → HCID 71268189, compound

HRID 1519700Notes

Reaction equation

HRID 1519700 reaction equation
[CH3:1][NH2:2].CO.[I:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([NH:14][CH:15]([C:21]([O:23]CC)=O)[C:16]([O:18][CH2:19]C)=[O:17])=[O:13])=[CH:8][CH:7]=1>CO>[I:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:13])[NH:14][CH:15]([C:21]([NH:2][CH3:1])=[O:23])[C:16]([O:18][CH3:19])=[O:17])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 11509661Diethyl {[(4-iodophenyl)carbonyl]amino}propandioateHCID 57454252Monomethylamine methanol2×

Product 1

HCID 71268189HCID 71268189, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 40% methylamine-methanol solution (0.80 mL) was added to a methanol (90 mL) solution of diethyl {[(4-iodophenyl)carbonyl]amino}propandioate (4.1 g) obtained by the same method as the synthesis method described in the literature (Organic & Biomolecular Chemistry, 2005, Vol. 3(19), pp. 3531-3539), and the mixture was stirred for 19 hours at room temperature. Further, a 40% methylamine-methanol solution (0.24 mL) was added, and the mixture was stirred for 19 hours at the same temperature, followed by concentrating the reaction mixture. The resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/ethanol=95/5→90/10) to obtain 1-iodo-4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl]carbamoyl}benzene (white solid) (1.5 g, 39%).

Workup

  1. customobtained by the same method as the synthesis method
  2. stirringthe mixture was stirred for 19 hours at the same temperature
  3. concentrationby concentrating the reaction mixture
  4. customThe resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/ethanol=95/5→90/10)

Sources & evidence

ORD record
ord-8eaa47e63ca04856ab22c5f5e89a2bbf
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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