Pyridine → HCID 13206714, compound

HRID 358107Notes

Reaction equation

HRID 358107 reaction equation
Cl.[C:2]([CH:5]([O:27][CH3:28])[C:6]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]3[N:21]([CH:22]=2)[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[S:18]3)[CH:12]=[CH:13][CH:14]=1)=[O:7])([OH:4])=[O:3].N1C=CC=CC=1.C(OCC)(=O)C>C(O)(=O)C>[C:2]([CH:5]([O:27][CH3:28])[C:6]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]3[N:21]([CH:22]=2)[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[S:18]3)[CH:12]=[CH:13][CH:14]=1)=[O:7])([OH:4])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 20450403HCID 20450403, compound2×

Product 1

HCID 13206714HCID 13206714, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

By following the same procedure as in Example 6 using 3.7 g of methoxymalonic acid mono-tert-butyl ester and 5 g of 2-(m-hydroxyphenyl)imidazo[2,1-b]benzothiazole, 6 g of 2-[m-(α-carboxy-α-methoxyacetoxy)phenyl]imidazo[2,1-b]benzothiazole.hydrochloride was obtained through 2-[m-(α-tert-butoxycarbonyl-α-methoxyacetoxy)phenyl]imidazo[2,1-b]benzothiazole (yield 7.3 g). Then, to 3 g of the hydrochloride were added a small amount of pyridine and 50 ml of ethyl acetate to dissolve the hydrochloride and 10% acetic acid was added to the solution, thereby crystals precipitated. The crystals thus formed were recovered by filtration, washed with isopropanol, and dried to provide 2.1 g of 2-[m-(α-carboxy-α-methoxyacetoxy)phenyl]imidazo[2,1-b]benzothiazole.

Workup

  1. additionwas added to the solution
  2. customcrystals precipitated
  3. customThe crystals thus formed
  4. filtrationwere recovered by filtration
  5. washwashed with isopropanol
  6. customdried

Sources & evidence

ORD record
ord-71d1e44fec524f618912534ee3796c4f
Source dataset
uspto-grants-1984_08
Patent number
US04464384

Reaction notes

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