Ethyl orthoformate → HCID 178498760, compound

HRID 1848065Notes

Reaction equation

HRID 1848065 reaction equation
[NH2:1][C:2]1[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:13](OC(OCC)OCC)C>C(O)=O>[N:1]1[C:2]2[C:3](=[N:4][CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=2)[NH:12][CH:13]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 9920476Methyl 5,6-diaminopyridine-3-carboxylate

Product 1

HCID 178498760HCID 178498760, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of methyl 5,6-diaminonicotinate (1.69 g, 10.12 mmol) from Step 1 of this Example, formic acid (0.5 mL), and triethylorthoformate (25 mL) was heated at 90° C. for 2.5 h. The reaction mixture was cooled to rt and then the precipitated solid was collected by filtration and dried to afford methyl 3H-imidazo[4,5-b]pyridine-6-carboxylate (588 mg, 33%) as a cream solid which did not require further purification. The filtrate was concentrated under reduced pressure, and the residue purified by silica gel flash chromatography eluting with 100% DCM to 10% MeOH in DCM to afford additional methyl 3H-imidazo[4,5-b]pyridine-6-carboxylate (550 mg, 31%) as a cream solid. 1H NMR (300 MHz, DMSO-d6) δ 13.33 (br s, 1H), 8.95 (d, J=1.5 Hz, 1H), 8.64 (s, 1H), 8.50 (d, J=1.5 Hz, 1H), 3.91 (s, 3H). LCMS (ESI) m/z 178 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationthe precipitated solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-5a9a4ed860a546edac3ac5ced7b126e5
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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