Réaction #1509597

ord-a15aac5b07ea49c6bd015a4ccf3331e2

Équation de réaction

CNC
dimethylamine
Cc1cc(C(=O)O)cc(Cl)n1
2-Chloro-6-methyl-isonicotinic acid
CCN(C(C)C)C(C)C
DIPEA
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
→
Cc1cc(C(=O)N(C)C)cc(Cl)n1
title compound
Cc1cc(C(=O)N(C)C)cc(Cl)n1
2-Chloro-6,N,N-trimethyl-isonicotinamide

Réactifs

CNC
dimethylamine
Cc1cc(C(=O)O)cc(Cl)n1
2-Chloro-6-methyl-isonicotinic acid
CCN(C(C)C)C(C)C
DIPEA
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU

Réactifs

Aucun

Solvants

O
water
CN(C)C=O
DMF

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionextracted with EtOAc
  2. 2
    AutreThe organic layer was separated
  3. 3
    Autredried
  4. 4
    Concentrationconcentrated in vacuum

Mode opératoire

To a solution of 2-Chloro-6-methyl-isonicotinic acid (1 g) in DMF (200 ml) at 25° C. was added DIPEA (2.9 mL) and TBTU (1.8 ml). After 5 min, dimethylamine (0.75 g) was added dropwise. This was stirred overnight. The reaction was added to water and extracted with EtOAc. The organic layer was separated, dried and concentrated in vacuum. Flash:chromatography (9:1 to 2:8 gradient cyclohexane:EtOAc) afforded the title compound (320 mg). Rf=0.56 (1:1 cyclohexane:EtOAc)

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: USRE045323E1uspto-grants-2015_01