Reaction #1256760

ord-9513aa9f12114713be87be169911f7f0

Reaction equation

N#Cc1c(-c2ccc(N)cc2)cc(C2CC2)nc1OS(=O)(=O)C(F)(F)F
trifluoromethanesulphonic acid 4-(4-amino-phenyl)-3-cyano-6-cyclopropyl-pyridin-2-yl ester
O=C=Nc1ccccc1F
1-fluoro-2-isocyanato-benzene
→
N#Cc1c(-c2ccc(NC(=O)Nc3ccccc3F)cc2)cc(C2CC2)nc1OS(=O)(=O)C(F)(F)F
product
Yield 66.0%
N#Cc1c(-c2ccc(NC(=O)Nc3ccccc3F)cc2)cc(C2CC2)nc1OS(=O)(=O)C(F)(F)F
Trifluoromethanesulphonic acid 3-cyano-6-cyclopropyl-4-{4-[3-(2-fluoro-phenyl)-ureido]-phenyl}-pyridin-2-yl ester
Yield 66.0%

Reactants

N#Cc1c(-c2ccc(N)cc2)cc(C2CC2)nc1OS(=O)(=O)C(F)(F)F
trifluoromethanesulphonic acid 4-(4-amino-phenyl)-3-cyano-6-cyclopropyl-pyridin-2-yl ester
O=C=Nc1ccccc1F
1-fluoro-2-isocyanato-benzene

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

In analogy to GP 4, reaction of 200 mg trifluoromethanesulphonic acid 4-(4-amino-phenyl)-3-cyano-6-cyclopropyl-pyridin-2-yl ester (0.522 mmol) and 71 μl 1-fluoro-2-isocyanato-benzene yielded 179 mg product (0.343 mmol, 66% yield).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07825114B2uspto-grants-2010_11