Triethylamine → 4-Chloro-6-methoxy-1,5-naphthyridine-3-carbonitrile

HRID 638977Notes

Reaction equation

HRID 638977 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH2:16])=O.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:16]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 685767374-Chloro-6-(methyloxy)-1,5-naphthyridine-3-carboxamide

Product 1

HCID 685791014-Chloro-6-methoxy-1,5-naphthyridine-3-carbonitrileYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-chloro-6-(methyloxy)-1,5-naphthyridine-3-carboxamide (647 mg, 2.7 mmol) in anhydrous DCM (2 mL) with triethyamine (2 mL) at 0° C. was added trifluororacetic anhydride (1 mL) slowly. The resulting solution was warmed up to 25° C. and stirred for 1 h. The mixture was partitioned between CHCl and H2O. The aqueous layer was extracted several times with CHCl. The organic fractions were combined, concentrated and purified with column chromatography (silica, 0-25% ethyl acetate/hexane) affording the title compound as an off-white solid (540 mg, 91%): LC/MS (ES) m/e 220 (M+H)+.

Workup

  1. customThe mixture was partitioned between CHCl and H2O
  2. extractionThe aqueous layer was extracted several times with CHCl
  3. concentrationconcentrated
  4. custompurified with column chromatography (silica, 0-25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6e07b8488a3e49a1857584c7cca8b7f9
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

Loading…