Sodium Hydroxide → 4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amine

HRID 249300Notes

Reaction equation

HRID 249300 reaction equation
C([N:4]1[CH2:9][CH2:8][C:7]2[N:10]=[C:11]([NH2:13])[S:12][C:6]=2[CH2:5]1)(=O)C.[OH-].[Na+].[Cl-].[NH4+]>C(O)C>[NH2:13][C:11]1[S:12][C:6]2[CH2:5][NH:4][CH2:9][CH2:8][C:7]=2[N:10]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 25517Ammonium ChlorideHCID 150176501-(2-Amino-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl)-ethanone

Product 1

HCID 135196874H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amineYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5-Acetyl-2-amino-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridine (110 mg, 0.51 mmol) was dissolved in ethanol (1 ml) and treated with sodium hydroxide (15.4 mg, 0.38 mmol) in ethanol (1 ml). The solution was heated to 100° for 16 hours, then treated with additional sodium hydroxide (25.6 mg, 0.64 mmol) and heated to reflux for an additional 16 hours. Solid ammonium chloride was added, and the mixture was filtered and concentrated in vacuo. The residue was dissolved in chloroform, dried over sodium sulfate and solvent was removed, leaving the title product (67.4 mg, 0.43 mmol, 84% yield) as a yellow solid, which was used without further purification.

Workup

  1. temperatureThe solution was heated to 100° for 16 hours
  2. temperatureheated
  3. temperatureto reflux for an additional 16 hours
  4. filtrationthe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in chloroform
  7. dry with materialdried over sodium sulfate and solvent
  8. customwas removed

Sources & evidence

ORD record
ord-f751b7fa37104519b5a9cfab85ed765e
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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