1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 70236790, compound

HRID 650245Notes

Reaction equation

HRID 650245 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:14](=[O:15])[N:13]([CH:16]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:17][CH2:18][C:19]([NH:21][CH2:22][C:23]2[CH:24]([OH:37])[C:25](=[O:36])[CH:26]=[CH:27][C:28]=2[N:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]2=[O:35])=[O:20])[C:12]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[N:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>CS(C)=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[C:14](=[O:15])[N:13]([CH:16]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:17][CH2:18][C:19]([NH:21][CH2:22][C:23]2[C:24](=[O:37])[C:25](=[O:36])[CH:26]=[CH:27][C:28]=2[N:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]2=[O:35])=[O:20])[C:12]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[N:11][CH:10]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9813011pyridine TFAHCID 70239667HCID 70239667, compound

Product 1

HCID 70236790HCID 70236790, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(5-t-Butyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydropyrimidine-1-yl)-N-{2-hydroxy-3-oxo-6-(2-oxo-1,2-dihydropyridine-1-yl)-1-phenylmethyl}hexylacetamide (115 mg, 0.18 mmol) was dissolved in dimethylsulfoxide (2 ml), under argon atmosphere, and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (103 mg, 0.54 mmol) and pyridinium trifluoroacetate (17 mg, 0.1 mmol) were added to it, and the mixture was stirred for 3.5 hours. The reaction solution was diluted with ethyl acetate and washed successively with distilled water and saturated saline. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol=30/1), and thereafter hexane was added to it to precipitate solid. The precipitated solid was collected by filtration whereby the title compound (96 mg, 83% yield) was obtained.

Workup

  1. washwashed successively with distilled water and saturated saline
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol=30/1)
  5. additionhexane was added to it
  6. customto precipitate solid

Sources & evidence

ORD record
ord-0da8360ac72240a786ae5c4c0371261d
Source dataset
uspto-grants-2001_08
Patent number
US06271238B1

Reaction notes

Loading…