Ethyl iodoacetate → Ethyl {[6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3,5-dicyano-4-(piperidin-1-yl)pyridin-2-yl]oxy}acetate

HRID 2369214Notes

Reaction equation

HRID 2369214 reaction equation
I[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[C:18]([CH2:20][S:21][C:22]3[C:27]([C:28]#[N:29])=[C:26]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[C:25]([C:36]#[N:37])=[C:24]([OH:38])[N:23]=3)[N:19]=2)=[CH:11][CH:10]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Ag+2]>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[S:16][CH:17]=[C:18]([CH2:20][S:21][C:22]3[N:23]=[C:24]([O:38][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:25]([C:36]#[N:37])=[C:26]([N:30]4[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]4)[C:27]=3[C:28]#[N:29])[N:19]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 2

HCID 12183Ethyl iodoacetateHCID 178510526HCID 178510526, compound

Product 1

HCID 70908326Ethyl {[6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3,5-dicyano-4-(piperidin-1-yl)pyridin-2-yl]oxy}acetate

Reagents, catalysts & solvents 4

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

43 mg ethyl iodoacetate are initially charged in 2.4 ml of dry toluene. 47 mg (0.10 mmol) of the compound from Example 10A and 14 mg (0.05 mmol) of silver carbonate are then added. The reaction mixture is stirred with exclusion of light for 24 h. The mixture is then diluted with 1 ml of ethyl acetate, and 1 ml of saturated aqueous sodium bicarbonate solution is added. After separation of the phases the organic phase is dried over magnesium sulfate. The solvent is removed on a rotary evaporator and the residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. additionis added
  2. customAfter separation of the phases the organic phase
  3. dry with materialis dried over magnesium sulfate
  4. customThe solvent is removed on a rotary evaporator
  5. customthe residue is 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-c8455c0fb05242978f1bbc546eb6d4ea
Source dataset
uspto-grants-2014_04
Patent number
US08703934B2

Reaction notes

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