2-(Oxiran-2-ylmethoxy)benzonitrile → 1,4-Dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{{{2-{{p-{2-[3-(o-cyanophenoxy)-2-hydroxypropylamino]-2-methylpropoxy}-phenoxy}}-ethyl}}}-ester 5-methyl ester

HRID 620085Notes

Reaction equation

HRID 620085 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-:39])=[O:38])[CH:32]=2)[C:7]([C:13]([O:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([NH2:30])([CH3:29])[CH3:28])=[CH:21][CH:20]=2)=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4].[O:40]1[CH2:52][CH:41]1[CH2:42][O:43][C:44]1[CH:51]=[CH:50][CH:49]=[CH:48][C:45]=1[C:46]#[N:47]>C(O)(C)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-:39])=[O:38])[CH:32]=2)[C:7]([C:13]([O:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([NH:30][CH2:52][CH:41]([OH:40])[CH2:42][O:43][C:44]3[CH:51]=[CH:50][CH:49]=[CH:48][C:45]=3[C:46]#[N:47])([CH3:29])[CH3:28])=[CH:21][CH:20]=2)=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4]

Participants

4

Reactant 2

HCID 126196712-(Oxiran-2-ylmethoxy)benzonitrileHCID 703937091,4-Dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{2-[p-(2-amino-2-methylpropoxy)-phenoxy]-ethyl}-ester 5-methyl ester

Product 1

HCID 867429121,4-Dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{{{2-{{p-{2-[3-(o-cyanophenoxy)-2-hydroxypropylamino]-2-methylpropoxy}-phenoxy}}-ethyl}}}-ester 5-methyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 5.4 g (10 mmol) of 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{2-[p-(2-amino-2-methylpropoxy)-phenoxy]-ethyl}-ester 5-methyl ester and 2.3 g (13 mmol) of 2-(2,3-epoxypropoxy)-benzonitrile in 30 ml of isopropanol is heated under reflux for 18 hours. After working up and chromatography analogously to Example 1, 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{{{2-{{p-{2-[3-(o-cyanophenoxy)-2-hydroxypropylamino]-2-methylpropoxy}-phenoxy}}-ethyl}}}-ester 5-methyl ester is obtained in the form of an amorphous solid.

Workup

  1. temperatureunder reflux for 18 hours

Sources & evidence

ORD record
ord-9bc831b1beec47358a092ea96d2b9970
Source dataset
uspto-grants-1989_04
Patent number
US04818766

Reaction notes

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