Reaktion #314765

ord-660867e722d8439dac520a236d594069

Reaktionsgleichung

Cc1ncnc(C(=O)[O-])c1N.[Na+]
material
Cc1ncnc(C(=O)[O-])c1N.[Na+]
5-amino-6-methyl-4-pyrimidinecarboxylic acid monosodium salt
CS(=O)(=O)Cl
methanesulfonyl chloride
CS(=O)(=O)Cl
methanesulfonyl chloride
O=C(O)c1cc(Cl)nn1-c1ncccc1Cl
3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-carboxylic acid
O=C(O)c1cc(Cl)nn1-c1ncccc1Cl
3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid
CCN(CC)CC
triethylamine
CCN(CC)CC
triethylamine
CNC(=O)c1ncnc(C)c1NC(=O)c1cc(Cl)nn1-c1ncccc1Cl
title compound
Ausbeute 22.2%
CNC(=O)c1ncnc(C)c1NC(=O)c1cc(Cl)nn1-c1ncccc1Cl
5-[[[3-Chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]-N,6-dimethyl-4-pyrimidinecarboxamide
Ausbeute 22.2%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationFiltration

Vorschrift

To a solution of 0.26 mL (3.3 mmol) of methanesulfonyl chloride in 18 mL of acetonitrile at 0° C. was added 0.77 g (3.0 mmol) of 3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-carboxylic acid from Step J. 0.42 mL (3.0 mmol) of triethylamine in 9 mL of acetonitrile was added dropwise. After 20 minutes at 0° C., 0.525 g (3.0 mmol) of material from Step F was added. After 15 minutes 0.42 mL (3.0 mmol) of triethylamine was added dropwise. After 2 hours 0.26 mL (3.3 mmol) of methanesulfonyl chloride was added. After stirring overnight. The reaction mixture was poured into water. Filtration afforded 0.27 g of the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07560564B2uspto-grants-2009_07