2,2,6,6-Tetramethylpiperidine → HCID 86647122, compound

HRID 2391725Notes

Reaction equation

HRID 2391725 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[CH:9][NH:10][C:4]=2[CH:3]=1.CC1(C)CCCC(C)(C)N1.Cl[C:22]1([C:28]([O:30][CH3:31])=[O:29])[C:26](=[O:27])[CH:25]=[CH:24][S:23]1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]([C:24]3[S:23][C:22]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([OH:27])[CH:25]=3)[CH:9]=[N:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 130352,2,6,6-TetramethylpiperidineHCID 15588102Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylateHCID 178477829HCID 178477829, compound

Product 1

HCID 86647122HCID 86647122, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 0.68 g of 6-chloro-1H-imidazo[4,5-c]pyridine and 0.65 g of 2,2,6,6-tetramethylpiperidine in 100 ml chloroform were slowly added a solution of 0.87 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate in 40 ml chloroform. The reaction mixture was stirred for 12 h at room temperature. After washing with water (3×50 ml) the organic layer was separated, dried with MgSO4 and concentrated to a volume of about 100 ml. The residue was treated with n-hexane until precipitation takes place. The solid was filtered and the procedure was repeated once again. The combined solids were dried under vacuum to yield the title compounds as an isomeric mixture, which was used for the next step (example B3) without further purification.

Workup

  1. washAfter washing with water (3×50 ml) the organic layer
  2. customwas separated
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated to a volume of about 100 ml
  5. additionThe residue was treated with n-hexane until precipitation
  6. filtrationThe solid was filtered
  7. customThe combined solids were dried under vacuum

Sources & evidence

ORD record
ord-ad88f89f502344f3b288673bafe19577
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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