Dimethyl malonate → HCID 59184462, compound

HRID 424272Notes

Reaction equation

HRID 424272 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[CH3:12][O:13][C:14](=[O:20])[CH2:15][C:16](OC)=O>>[CH3:12][O:13][C:14](=[O:20])[CH2:15][C:16]1[NH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[S:8](=[O:10])(=[O:9])[N:11]=1

Participants

3

Reactant 2

HCID 7943Dimethyl malonateHCID 109759664-Amino-3-pyridinesulfonamide

Product 1

HCID 59184462HCID 59184462, compoundYield 37%

Conditions

Temperature
180 °C

Procedure

4-amino-pyridine-3-sulfonic acid amide (0.25 g, 1.44 mmol) was suspended in malonic acid dimethyl ester (5 mL, 43.75 mmol). The flask was purged with nitrogen and the mixture was stirred at 180° C. for 60 min. Upon cooling, the mixture was diluted with ethyl acetate (5 mL) causing immediate precipitation of an undesired side product. The solid was removed by vacuum filtration and rinsed with ethyl acetate (2 mL). The filtrate was passed through a plug of silica gel, eluting with ethyl acetate followed by 5% methanol in ethyl acetate. The fractions containing the 5% methanol in ethyl acetate were combined and concentrated in vacuo to afford the desired product, (1,1-dioxo-1,4-dihydro-1λ6-pyrido[4,3-e][1,2,4]thiadiazin-3-yl)-acetic acid methyl ester (0.135 g, 0.529 mmol, 37%) as a yellow oil. LC-MS (ESI) calculated for C9H9N3O4S 255.03, found 256.0 [M+H+].

Workup

  1. customThe flask was purged with nitrogen
  2. temperatureUpon cooling
  3. additionthe mixture was diluted with ethyl acetate (5 mL)
  4. customprecipitation of an undesired side product
  5. customThe solid was removed by vacuum filtration
  6. washrinsed with ethyl acetate (2 mL)
  7. washeluting with ethyl acetate
  8. additionThe fractions containing the 5% methanol in ethyl acetate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5e0ad4a80484f1394a4fbd289d536f0
Source dataset
uspto-grants-2012_01
Patent number
US08101800B2

Reaction notes

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