6-Methoxy-3-pyridinylamine → HCID 178471946, compound

HRID 2178874Notes

Reaction equation

HRID 2178874 reaction equation
C(O[CH:4]=[C:5]([C:11](=[O:13])[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][N:17]=1>ClC1C=CC=CC=1>[CH3:14][O:15][C:16]1[N:17]=[CH:18][C:19]([NH:22][CH:4]=[C:5]([C:11](=[O:13])[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 811216-Methoxy-3-pyridinylamineHCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl ester

Product 1

HCID 178471946HCID 178471946, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of ethyl 2-(ethoxymethylene)-3-oxobutanoate (100 g, 0.54 mol) and 2-methoxy-5-aminopyridine (67 g, 0.54 mol) in chlorobenzene (500 mL) was heated at 135° C. for 4 h in a round bottomed flask that was equipped with a distillation apparatus to collect the ethanol generated during the reaction. The reaction mixture was cooled and concentrated and the residue was triturated in diethylether and filtered to obtain the desired product (120 g, 84%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 12.74 (d, 12.3 Hz, 1H), 8.35 (d, J=13.0 Hz, 1H), 8.07 (d, J=2.8 Hz, 1H), 7.55 (d, J=8.8, 2.9 Hz, 1H), 6.79 (d, J=8.8 Hz, 1H), 4.30 (q, J=7.1 Hz, 2H), 2.55 (s, 3H), 1.33 (t, J=7.1 Hz, 1H); ESI MS m/z 265 [M+H]+.

Workup

  1. customwas equipped with a distillation apparatus
  2. customto collect the ethanol
  3. customgenerated during the reaction
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated
  6. customthe residue was triturated in diethylether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d2f5ddbaf2fc4fda82c038c74658d278
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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