Diisopropylethylamine → Methyl 6-(((3-butyl-5-methylisoxazol-4-yl)methyl)amino)nicotinate

HRID 1807544Notes

Reaction equation

HRID 1807544 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][NH2:11])=[C:8]([CH3:12])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].Cl[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][N:15]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([NH:11][CH2:10][C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH3:12])=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 66643513C-(3-Butyl-5-methyl-isoxazol-4-yl)-methylamine

Product 1

HCID 66643788Methyl 6-(((3-butyl-5-methylisoxazol-4-yl)methyl)amino)nicotinateYield 49%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

C-(3-Butyl-5-methyl-isoxazol-4-yl)-methylamine (320 mg, 1.90 mmol) was dissolved in DMSO (3 mL), methyl 6-chloronicotinate (326 mg, 1.90 mmol) and N,N-diisopropylethylamine (492 mg, 3.80 mmol) added, and the reaction mixture heated under microwave irradiation at 160° C. for 1 h. The reaction mixture was poured onto ice-water and extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated then purified by chromatography (silica, 0 to 50% ethyl acetate in heptane) to give the title compound (280 mg, 49%) as a white solid. MS: m/e=348.5 [M+H]+.

Workup

  1. additionThe reaction mixture was poured onto ice-water
  2. extractionextracted with ethyl acetate
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthen purified by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b2a7866101834f60a0ce45dff2f8d23f
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

Loading…