Diethyl Ether → N-[1-(alpha-(2-(2-(2-Methoxyethoxy)-ethoxy)-ethoxycarbonyloxy)benzyl)-1,4-dihydropyridin-4-ylidene]-N'-cyano-N''-(6-(4-chlorophenoxy)-hexyl)-guanidine

HRID 1060789Notes

Reaction equation

HRID 1060789 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH:22][C:23]#[N:24])=[N:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.[C:27](=[O:48])([O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH3:47])[O:28][CH:29](Cl)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCOC(C)=O.CCOCC>ClCCl>[CH3:47][O:46][CH2:45][CH2:44][O:43][CH2:42][CH2:41][O:40][CH2:39][CH2:38][O:37][C:27]([O:28][CH:29]([N:19]1[CH:20]=[CH:21][C:16](=[N:15][C:14]([NH:22][C:23]#[N:24])=[N:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][C:5]2[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:17]=[CH:18]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:48]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 8857Ethyl AcetateHCID 18629469alpha-Chlorobenzyl 2-(2-(2-methoxyethoxy)-ethoxy)-ethyl carbonateHCID 178512290Chs-828

Product 1

HCID 10168663N-[1-(alpha-(2-(2-(2-Methoxyethoxy)-ethoxy)-ethoxycarbonyloxy)benzyl)-1,4-dihydropyridin-4-ylidene]-N'-cyano-N''-(6-(4-chlorophenoxy)-hexyl)-guanidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(6-(4-chlorophenoxy)-hexyl)-N′-cyano-N″-(4-pyridyl)-guanidine (67 mg) and α-chlorobenzyl 2-(2-(2-methoxyethoxy)-ethoxy)-ethyl carbonate (150 mg) was placed in a preheated oil bath at 90° C. After 10 minutes a clear yellow melt was formed and after a further 20 minutes the mixture was cooled to room temperature and EtOAc (4 ml) was added. Decantation and evaporation in vacuo gave a residue which was treated with ether. After decantation of the ether, the residue was taken up in dichloromethane and washed with an excess of sodium bicarbonate. Chromatography on silica gel with dichloromethane/methanol (98:2) as eluent gave the title compound as a colourless oil.

Workup

  1. customwas placed in a preheated oil bath at 90° C
  2. customAfter 10 minutes a clear yellow melt was formed and after a further 20 minutes the mixture
  3. customDecantation and evaporation in vacuo
  4. customgave a residue which
  5. washwashed with an excess of sodium bicarbonate

Sources & evidence

ORD record
ord-5e422d87fc5f4d0882780eb4bd096495
Source dataset
uspto-grants-2003_02
Patent number
US06525077B2

Reaction notes

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