Imidazole → HCID 67485925, compound

HRID 1809633Notes

Reaction equation

HRID 1809633 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([O:9][C:10]2[C:11]([C:23]([NH2:25])=[O:24])=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.N1C=CN=C1.[C:31]([Si:35](Cl)([CH3:37])[CH3:36])([CH3:34])([CH3:33])[CH3:32]>C(Cl)Cl>[Si:35]([O:1][CH2:2][C:3]1[C:8]([O:9][C:10]2[C:11]([C:23]([NH2:25])=[O:24])=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67485696HCID 67485696, compound

Product 1

HCID 67485925HCID 67485925, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-(Hydroxymethyl)pyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide (575 mg, 1.62 mmol) was dissolved in CH2Cl2 (20 mL) and 1H-imidazole (166 mg, 2.43 mmol) and tert-butylchlorodimethylsilane (293 mg, 1.95 mmol) were added. The reaction was stirred at ambient temperature for 2 hours. The solids were filtered and the filtrate was concentrated. The residue was purified on silica gel (5% methanol in EtOAc) to afford 3-(2-((tert-butyldimethylsilyloxy)methyl)pyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide (391 mg, 0.834 mmol, 51.4% yield).

Workup

  1. filtrationThe solids were filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified on silica gel (5% methanol in EtOAc)

Sources & evidence

ORD record
ord-ad8c024bbe724ecb96591ef788263365
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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