2-(Oxiran-2-ylmethoxy)benzonitrile → HCID 70393792, compound

HRID 620082Notes

Reaction equation

HRID 620082 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=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][CH2:27][NH2:28])=[CH:21][CH:20]=2)=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4].[O:38]1[CH2:50][CH:39]1[CH2:40][O:41][C:42]1[CH:49]=[CH:48][CH:47]=[CH:46][C:43]=1[C:44]#[N:45]>C(O)(C)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=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][CH2:27][NH:28][CH2:50][CH:39]([OH:38])[CH2:40][O:41][C:42]3[CH:49]=[CH:48][CH:47]=[CH:46][C:43]=3[C:44]#[N:45])=[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 70393778HCID 70393778, compound

Product 1

HCID 70393792HCID 70393792, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 3.5 g (6.8 mmol) of 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{2-[p-(2-aminoethoxy)-phenoxy]-ethyl}-ester 5-methyl ester and 1.55 g (8.9 mmol) of 2-(2,3-epoxypropoxy)-benzonitrile in 20 ml of isopropanol is heated under reflux for 2 hours. The oil obtained after concentration by evaporation (approximately 6 g) is purified by "flash" chromatography analogously to Example 1 and yields 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{{{2-{{p-{2-[3-(o-cyanophenoxy)-2-hydroxypropylamino]-ethoxy}-phenoxy}}-ethyl}}}-ester 5-methyl ester in the form of an amorphous solid.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe oil obtained
  3. concentrationafter concentration
  4. customby evaporation (approximately 6 g)
  5. customis purified by "flash" chromatography analogously to Example 1

Sources & evidence

ORD record
ord-98dc0da875f04e2690e515818e51623c
Source dataset
uspto-grants-1989_04
Patent number
US04818766

Reaction notes

Loading…