Sodium Bicarbonate → 2-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-6-methyl-4-(tetrahydro-2H-pyran-2-yl)-pyridine-3,5-dicarbonitrile

HRID 1873608Notes

Reaction equation

HRID 1873608 reaction equation
[CH3:1][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+].NC1C(C#N)=C(C2CCCCO2)C(C#N)=C(SCC2N=C(C3C=CC(Cl)=CC=3)SC=2)N=1>CN(C=O)C>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[S:24][CH:25]=[C:21]([CH2:20][S:18][C:4]3[C:5]([C:16]#[N:17])=[C:6]([CH:10]4[CH2:15][CH2:14][CH2:13][CH2:12][O:11]4)[C:7]([C:8]#[N:9])=[C:2]([CH3:1])[N:3]=3)[N:22]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 24959059Rac-2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(tetrahydro-2h-pyran-2-yl)-pyridine-3,5-dicarbonitrileHCID 178433544HCID 178433544, compound

Product 1

HCID 686974352-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-6-methyl-4-(tetrahydro-2H-pyran-2-yl)-pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.14 mmol) of the compound from Example 41A, 40 mg (0.16 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 45 mg (0.54 mmol) of sodium bicarbonate are reacted in 2.8 ml of dry DMF analogously to the preparation of the compound of Example 14.

Sources & evidence

ORD record
ord-876749ec4581450ebcc6c43513a92540
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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