2,2,6,6-Tetramethylpiperidine → methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-hydroxythiophene-2-carboxylate

HRID 2391726Notes

Reaction equation

HRID 2391726 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][NH:18][C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC1(C)CCCC(C)(C)N1.Cl[C:30]1([C:36]([O:38][CH3:39])=[O:37])[C:34](=[O:35])[CH:33]=[CH:32][S:31]1>ClCCl.C(Cl)(Cl)Cl>[Si:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][N:18]([C:32]3[S:31][C:30]([C:36]([O:38][CH3:39])=[O:37])=[C:34]([OH:35])[CH:33]=3)[C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 130352,2,6,6-TetramethylpiperidineHCID 15588102Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylateHCID 178455113HCID 178455113, compound

Product 1

HCID 68766707methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-hydroxythiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 21.2 g of 6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridine and 11.36 g of 2,2,6,6-tetramethylpiperidine in 2 l dichloromethane was slowly added a solution of 8.77 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate in 300 ml chloroform at 30-40° C. The reaction mixture was stirred for 12 h, washed with water (2×200 ml) and concentrated under vacuum. The residue was purified by flash chromatography (eluents: ethyl acetate/methanol/triethylamine) two times and after precipitation from ethyl acetate/n-hexane the title compounds were obtained as a mixture of regioisomers.

Workup

  1. washwashed with water (2×200 ml)
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash chromatography (eluents: ethyl acetate/methanol/triethylamine) two times
  4. customafter precipitation from ethyl acetate/n-hexane the title compounds
  5. customwere obtained as a mixture of regioisomers

Sources & evidence

ORD record
ord-eff5667c642445309ab10ddfec747138
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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