Potassium Carbonate → HCID 44548548, compound

HRID 1630728Notes

Reaction equation

HRID 1630728 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]([O:22][CH3:23])[N:3]=1.[S-2:24].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40]Cl)[CH:35]=1>CN(C=O)C>[OH:19][CH2:18][CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:6]2[C:7]([C:8]#[N:9])=[C:2]([S:24][CH2:40][C:36]3[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=3)[N:3]=[C:4]([O:22][CH3:23])[C:5]=2[C:20]#[N:21])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14804Sodium SulfideHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 86654213HCID 86654213, compound

Product 1

HCID 44548548HCID 44548548, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

494 mg (1.5 mmol) of 2-chloro-4-[4-(2-hydroxyethoxy)phenyl]-6-methoxypyridine-3,5-dicarbonitrile are initially charged in 5 ml of DMF, 140 mg (1.8 mmol) of sodium sulphide are added and the mixture is stirred at room temperature for 3 hours. 311 mg (2.25 mmol) of potassium carbonate and 307 mg (1.8 mmol) of 3-picolyl chloride hydrochloride are then added. The reaction mixture is stirred at 45° C. overnight and then purified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% formic acid added). This gives 255 mg (40% of theory) of the target compound.

Workup

  1. stirringThe reaction mixture is stirred at 45° C. overnight
  2. custompurified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% formic acid added)

Sources & evidence

ORD record
ord-00f9965224804a4c93abd2af6a47f460
Source dataset
uspto-grants-2014_07
Patent number
US08791146B2

Reaction notes

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