Reaktion #1509597

ord-a15aac5b07ea49c6bd015a4ccf3331e2

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Lösungsmittel

O
water
CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted with EtOAc
  2. 2
    SonstigeThe organic layer was separated
  3. 3
    Sonstigedried
  4. 4
    Einengenconcentrated in vacuum

Vorschrift

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)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE045323E1uspto-grants-2015_01