Sodium Bicarbonate → 2'-Amino-6'-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-6-(2-hydroxyethoxy)-3,4'-bipyridine-3',5'-dicarbonitrile

HRID 242171Notes

Reaction equation

HRID 242171 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[S:6][CH:7]=1.[NH2:15][C:16]1[C:21]([C:22]#[N:23])=[C:20]([C:24]2[CH:25]=[N:26][C:27]([O:30][CH2:31][CH2:32][OH:33])=[CH:28][CH:29]=2)[C:19]([C:34]#[N:35])=[C:18]([SH:36])[N:17]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:15][C:16]1[C:21]([C:22]#[N:23])=[C:20]([C:24]2[CH:25]=[N:26][C:27]([O:30][CH2:31][CH2:32][OH:33])=[CH:28][CH:29]=2)[C:19]([C:34]#[N:35])=[C:18]([S:36][CH2:2][C:3]2[N:4]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=3)[S:6][CH:7]=2)[N:17]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178510485HCID 178510485, compound

Product 1

HCID 247719802'-Amino-6'-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-6-(2-hydroxyethoxy)-3,4'-bipyridine-3',5'-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

63 mg (0.26 mmol) of 4-chloromethyl-2-(4-chlorphenyl)thiazole, 100 mg (0.23 mmol) of the compound from example 2A and 78 mg (0.93 mmol) of sodium bicarbonate are dissolved in 1.5 ml of DMF, and the reaction solution is stirred at RT for 20 h. The mixture is then filtered through a paper filter, and the filtrate is directly purified chromatographically by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). This gives the title compound as a beige solid.

Workup

  1. filtrationThe mixture is then filtered through a paper
  2. filtrationfilter
  3. customthe filtrate is directly purified chromatographically by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-35501c1970c14f32b5473510a3342985
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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