Sodium Bicarbonate → N-[2'-Amino-6'-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3',5'-dicyano-3,4'-bipyridin-6-yl]acetamide

HRID 242172Notes

Reaction equation

HRID 242172 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:14][CH:15]=2)[C:5]([C:20]#[N:21])=[C:4]([SH:22])[N:3]=1.Cl[CH2:24][C:25]1[N:26]=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[S:28][CH:29]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:14][CH:15]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:24][C:25]2[N:26]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[S:28][CH:29]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178474089HCID 178474089, compound

Product 1

HCID 68584873N-[2'-Amino-6'-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3',5'-dicyano-3,4'-bipyridin-6-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15 mg (0.03 mmol) of the compound from example 20A are dissolved in 0.7 ml of dry DMF, and 10 mg (0.04 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 11 mg (0.14 mmol) of sodium bicarbonate are added. The reaction mixture is stirred at RT for 8 h. The mixture is then poured into 2 ml of saturated aqueous sodium bicarbonate solution, and the aqueous phase is extracted three times with in each case 5 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate, and the solvent is removed on a rotary evaporator.

Workup

  1. extractionthe aqueous phase is extracted three times with in each case 5 ml of ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-b2415088b6aa4ef8a8b95ea88bcf5a31
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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