Pyridine → 2-Methoxycarbonylaminothiazolo[4,5-c]pyridine

HRID 615798Notes

Reaction equation

HRID 615798 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[CH3:11][O:12][C:13](Cl)=[O:14].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:11][O:12][C:13]([NH:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1)=[O:14]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 14252938(1,3)Thiazolo(4,5-c)pyridin-2-amine

Product 1

HCID 155935482-Methoxycarbonylaminothiazolo[4,5-c]pyridineYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-aminothiazolo[4,5-c]pyridine (50 mg, 0.33 mmole) and 0.4 ml of methylchloroformate in 1 ml of dry DMF was added 0.4 ml of pyridine. The mixture was allowed to stand overnight at room temperature and aqueous NaHCO3 and ethyl acetate were then added. The organic layer was separated, washed with saturated aqueous NaCl solution, dried over Na2SO4 and evaporated in vacuo to give 54 mg (78%) of the title compound, which was recrystallized from CHCl3 --CH3OH to give pure crystalline solid. Mp 146°~152° C. (dec.).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-d341d400982c448e9e01cc8729749e99
Source dataset
uspto-grants-1985_02
Patent number
US04500526

Reaction notes

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