Methyl 5-amino-6-mercaptonicotinate → [1,2,3]Thiadiazolo[5,4-b]pyridine-6-carboxylic acid methyl ester

HRID 2214962Notes

Reaction equation

HRID 2214962 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([NH2:11])[C:8](=[S:12])[NH:7][CH:6]=1)=[O:4].[N:13]([O-])=O.[Na+]>Cl.O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]2[N:11]=[N:13][S:12][C:8]2=[N:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 11458085Methyl 5-amino-6-mercaptonicotinateHCID 23668193Sodium Nitrite

Product 1

HCID 11469626[1,2,3]Thiadiazolo[5,4-b]pyridine-6-carboxylic acid methyl esterYield 65.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
-3 °C

Procedure

The amine (i) (1.3 g) was suspended in 0.5 M hydrochloric acid (200 mL) and cooled to −3° C. A solution of sodium nitrite (487 mg) in water (3 mL) was added dropwise over 10 minutes and the mixture was stirred for 2 hours when the solid product was collected and chromatographed on silica gel (chloroform) to afford a solid (0.90 g)

Workup

  1. customwas collected
  2. customchromatographed on silica gel (chloroform)

Sources & evidence

ORD record
ord-b89e3b55170045dd8253b4b36bce6dde
Source dataset
uspto-grants-2006_09
Patent number
US07109213B2

Reaction notes

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