Water → 2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-6-(diethylamino)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile

HRID 1968322Notes

Reaction equation

HRID 1968322 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[S:27][CH:28]=2)[N:3]=1.[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37].O>C1COCC1>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:26]2[S:27][CH:28]=[C:24]([CH2:23][S:22][C:4]3[C:5]([C:20]#[N:21])=[C:6]([C:10]4[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:15]=4)[C:7]([C:8]#[N:9])=[C:2]([N:38]([CH2:39][CH3:40])[CH2:36][CH3:37])[N:3]=3)[N:25]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8021DiethylamineHCID 866438472-Chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile

Product 1

HCID 468530212-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-6-(diethylamino)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At RT, 60 mg (0.11 mmol) of 2-chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile (Example 2A) and 0.023 ml (0.22 mmol) of diethylamine were stirred in 1.5 ml of THF for 30 min. About 15 ml of water were added to the reaction mixture, and the aqueous phase was extracted 3× with ethyl acetate. The combined organic phases were washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, concentrated by evaporation and dried under high vacuum. This gave 67 mg (99% of theory, purity 95%) of the desired target compound.

Workup

  1. extractionthe aqueous phase was extracted 3× with ethyl acetate
  2. washThe combined organic phases were washed once with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-f4d686234fd5416d8575d16be7056395
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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