1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → HCID 178456821, compound

HRID 2227180Notes

Reaction equation

HRID 2227180 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([NH2:10])[CH:4]=1)#[N:2].[CH:11]([N:14]=[C:15]=S)([CH3:13])[CH3:12].CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CCN=C=NC2CCCCC2)CCOCC1>N1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]2[NH:9][C:15]([NH:14][CH:11]([CH3:13])[CH3:12])=[N:10][C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 75263Isopropyl IsothiocyanateHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 178456821HCID 178456821, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Cyano-1,2-phenylenediamine (prepared according to the method of Fairley, T. A., et.al. J. Med. Chem. 1993, 36, 1746, 3.7 g, 27.8 mmol), isopropyl isothiocyanate (3.3 g, 32.7 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (16.0 g , 37.8 mmol) and pyridine (200 mL) were used according to general procedure I. The title compound was recrystallized from 1,4-dioxane to provide a tan powder (2.2 g, 40%); m.p. 185-190° C.; 1H NMR (DMSO-d6) δ: 11.0 (br s, 1H, NH), 7.44 (s, 1H, Ar—H), 7.2-7.1 (m, 2H, Ar—H), 6.95 (br s, 1H, NH), 3.88 (m, 1H, CH), 1.16 (d, J=6.5 Hz, 6H, overlapping CH3).

Workup

  1. customThe title compound was recrystallized from 1,4-dioxane

Sources & evidence

ORD record
ord-303475736baa4314b7e7e0b1ce348809
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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