ChemicalBook CAS DataBase List 3H-IMidazo[4,5-c]pyridine-6-carboxylic acid, Methyl ester

3H-IMidazo[4,5-c]pyridine-6-carboxylic acid, Methyl ester synthesis

9synthesis methods

Product Name:3H-IMidazo[4,5-c]pyridine-6-carboxylic acid, Methyl ester
CAS Number:82523-07-7
Molecular formula:C8H7N3O2
Molecular Weight:177.16

(S)-Methyl 4,5,6,7-tetrahydro-3h-iMidazo[4,5-c]pyridine-6-carboxylate DiHCl

114786-39-9

121-44-8

3H-IMidazo[4,5-c]pyridine-6-carboxylic acid, Methyl ester

82523-07-7

The general procedure for the synthesis of methyl 3H-imidazo[4,5-c]pyridine-6-carboxylate from (S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester dihydrochloride (156.5 g, 0.62 mol) and triethylamine (445.0 g, 4.4 mol, 7.0 equiv) was as follows: selenium dioxide ( 158.2 g, 1.43 mol, 2.3 equiv) and polyphosphoric acid methyl ether (PPSE) (15.0 g) were added to carbon tetrachloride (CCl4) (1.5 L). After cooling to room temperature, the mixture was refluxed for 6 hours. After completion of the reaction, the solvent was removed under reduced pressure and the residue was suspended in methanol (1.5 L) and the pH was adjusted to 8 by addition of triethylamine. the brown solid was collected by filtration and washed well with methanol. The resulting brown solid (117.0 g) was recrystallized. The product was dissolved in hot N,N-dimethylformamide (DMF) (2 L) and hot filtered to remove the black selenium salt by-product. After cooling to room temperature, the target product crystallized as a yellow solid (51.3 g, 47% yield, 95% purity). The product was characterized as follows: 1H NMR (DMSO-d6): δ 13.20 (br s, 1H), 9.02 (s, 1H), 8.58 (s, 1H), 8.31 (s, 1H), 3.89 (s, 3H); LCMS: Rt = 1.33 min, [M + 1]+ = 178.1 m/z.

1H-Imidazo[4,5-c]pyridine-6-carboxylic acid, 4,5,6,7-tetrahydro-, methyl ester, (6S)-

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82523-07-7
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Yield:82523-07-7 82%

Reaction Conditions:

with potassium permanganate;triethylamine in N,N-dimethyl-formamide; pH=8; for 12 h;

Steps:

3 Example 3 Preparation of 3H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester

4 g (22.1 mmol) of (6S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester200 mL of dimethylformamide was dissolved, and the pH was adjusted to 8 with triethylamine.500mg KMnO4 was added in 3 times in an ice bath.Stir for 12 h.The reaction mixture was concentrated under reduced vacuo.The insoluble matter was removed by filtration. The filtrate was adjusted to pH 7 with an aqueous NaOH solution in an ice bath.The colorless solid was filtered after analysis. The filter cake was washed with distilled water and allowed to dry at room temperature.Having 3.715 g (82%) of the title compound,It is a colorless solid.

References:

CN108976225,2018,A Location in patent:Paragraph 0025; 0026

114786-39-9
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121-44-8 Synthesis

121-44-8
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82523-07-7
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References

82523-06-6 Synthesis