1,2-Dichloroethane → 3-Ethyl 5-methyl 2-((2-methoxyethyl)amino)-6-methyl-4-(p-tolyl)pyridine-3,5-dicarboxylate

HRID 1912594Notes

Reaction equation

HRID 1912594 reaction equation
F[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:5]([C:20]([O:22][CH3:23])=[O:21])=[C:4]([CH3:24])[N:3]=1.[CH3:25][O:26][CH2:27][CH2:28][NH2:29].CCN(C(C)C)C(C)C.ClCCCl>C(=O)(O)[O-].[Na+]>[CH3:25][O:26][CH2:27][CH2:28][NH:29][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:5]([C:20]([O:22][CH3:23])=[O:21])=[C:4]([CH3:24])[N:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 71209155Ethyl 5-methyl 2-fluoro-6-methyl-4-(p-tolyl)pyridine-3,5-dicarboxylate

Product 1

HCID 712094393-Ethyl 5-methyl 2-((2-methoxyethyl)amino)-6-methyl-4-(p-tolyl)pyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

3-Ethyl 5-methyl 2-fluoro-6-methyl-4-(p-tolyl)pyridine-3,5-dicarboxylate (500 mg, 1.51 mmol) (Example 73, Step A), 2-methoxyethanamine (5 eq., 7.55 mmol, 0.65 mL), DIPEA (2 eq. 3.02 mmol, 0.53 mL) and DCE (5 mL) were combined and heated in a microwave reactor set at 140° C. for 1 hour. The mixture was diluted with saturated sodium bicarbonate solution, extracted with DCM, dried over sodium sulfate and purified by silica-gel chromatography to give the title compound to Step A (285 mg, 49%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=7.49 (m, 1 H), 7.12 (m, 2 H), 7.03 (m, 2 H), 3.85 (m, 2 H), 3.74 (m, 2 H), 3.60 (m, 2 H), 3.44-3.40 (m, 6 H), 2.44 (s, 3 H), 2.35 (s, 3 H), 0.67 (m, 3 H); LCMS (m/z) ES+=387.33 (M+1).

Workup

  1. temperatureheated in a microwave reactor
  2. extractionextracted with DCM
  3. dry with materialdried over sodium sulfate
  4. custompurified by silica-gel chromatography

Sources & evidence

ORD record
ord-3e8536b75ca34fb1a4795a2fde32e3d3
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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