1-Propanol → 2-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-phenyl-6-propoxypyridine-3,5-dicarbonitrile

HRID 1630720Notes

Reaction equation

HRID 1630720 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].CC(C)([O-])C.[K+].Cl[C:12]1[C:17]([C:18]#[N:19])=[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([C:26]#[N:27])=[C:14]([S:28][CH2:29][C:30]2[N:31]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[S:33][CH:34]=2)[N:13]=1>CN(C=O)C>[Cl:41][C:38]1[CH:37]=[CH:36][C:35]([C:32]2[S:33][CH:34]=[C:30]([CH2:29][S:28][C:14]3[C:15]([C:26]#[N:27])=[C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:17]([C:18]#[N:19])=[C:12]([O:4][CH2:1][CH2:2][CH3:3])[N:13]=3)[N:31]=2)=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 23665647Potassium tert-butoxideHCID 866542112-Chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-phenylpyridine-3,5-dicarbonitrile

Product 1

HCID 445481962-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-phenyl-6-propoxypyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

37 μl (0.501 mmol) of 1-propanol are initially charged in 2 ml of DMF, 20 mg (0.184 mmol) of potassium tert-butoxide are added and the mixture is stirred for 15 minutes, after which 100 mg (0.167 mmol) of 2-chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-phenylpyridine-3,5-dicarbonitrile, dissolved in 2 ml of DMF, are added. The reaction mixture is stirred at room temperature for one hour and then purified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% TFA added). This gives 13 mg (15% of theory) of the target compound.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred at room temperature for one hour
  3. custompurified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% TFA added)

Sources & evidence

ORD record
ord-317eb3888ae248fe9a7b6dd3330bb280
Source dataset
uspto-grants-2014_07
Patent number
US08791146B2

Reaction notes

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