Sodium Bicarbonate → 2-Amino-4-[4-(2-hydroxyethoxy)phenyl]-6-{[(2-methyl-1,3-thiazol-4-yl)methyl]-sulphanyl}pyridine-3,5-dicarbonitrile

HRID 2214978Notes

Reaction equation

HRID 2214978 reaction equation
[NH2:1][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]([SH:22])[N:3]=1.[C:23](=O)(O)[O-].[Na+].Cl.[CH3:29][C:30]1[N:31]=[C:32](Cl)[S:33][CH:34]=1>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:15]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:29][C:30]2[N:31]=[C:32]([CH3:23])[S:33][CH:34]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 219490854-Methyl-2-chloro-1,3-thiazole hydrochlorideHCID 178510483HCID 178510483, compound

Product 1

HCID 219490802-Amino-4-[4-(2-hydroxyethoxy)phenyl]-6-{[(2-methyl-1,3-thiazol-4-yl)methyl]-sulphanyl}pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

31.2 mg (0.1 mmol) of 2-amino-4-[4-(2-hydroxyethoxy)phenyl]-6-sulphanyl-pyridine-3,5-dicarbonitrile are dissolved in 0.3 ml of DMF. 33.6 mg (0.4 mmol) of sodium bicarbonate and 26.7 mg (0.15 mmol) of 4-methyl-2-chloro-1,3-thiazole hydrochloride are then added. The suspension is shaken at RT overnight, filtered, and purified by preparative HPLC [column: Macherey-Nagel VP 50/21 Nucleosil 100-5 C18 Nautilus, 20×50 mm; flow rate: 25 ml/min; gradient (A=acetonitrile, B=water+0.3% trifluoroacetic acid): 0 min 10% A; 2.0 min 10% A; 6.0 min 90% A; 7.0 min 90% A; 7.1 min 10% A; 8.0 min 10% A; detection: 220 nm]. Concentration of the appropriate fraction gives 20.2 mg (47.7% of theory) of product.

Workup

  1. filtrationfiltered
  2. custompurified by preparative HPLC [column
  3. custom0 min 10% A
  4. custom2.0 min 10% A
  5. custom6.0 min 90% A
  6. custom7.0 min 90% A
  7. custom7.1 min 10% A
  8. custom8.0 min 10% A
  9. customConcentration of the appropriate fraction gives 20.2 mg (47.7% of theory) of product

Sources & evidence

ORD record
ord-e7bb3a6768fa4a3c99df7a884ac71859
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Reaction notes

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