Sodium Bicarbonate → Rac-2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(tetrahydro-2h-pyran-2-yl)-pyridine-3,5-dicarbonitrile

HRID 1873602Notes

Reaction equation

HRID 1873602 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:5]([C:16]#[N:17])=[C:4]([SH:18])[N:3]=1.Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[S:24][CH:25]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:20][C:21]2[N:22]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[S:24][CH:25]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178510477HCID 178510477, compound

Product 1

HCID 24959059Rac-2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(tetrahydro-2h-pyran-2-yl)-pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

33 mg (0.10 mmol) of the compound from Example 31A, 29 mg (0.12 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 33 mg (0.39 mmol) of sodium bicarbonate are suspended in 2 ml of dry DMF. The reaction mixture is stirred at RT for 20 h. The mixture is filtered and directly purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. filtrationThe mixture is filtered
  2. customdirectly purified 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-72e4fe90af954bdd9ffa43b940a5e950
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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