Reacción #85166

ord-1be502e86bd244e4b6544ad3b222d4d2

Ecuación de reacción

CC#N.O
acetonitrile water
COc1cn(C(CC2(C)COC2)C(=O)O)c(=O)cc1-c1cc(Cl)ccc1C#N
2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)propanoic acid
C=CCOC(=O)c1ccc(N)cc1
allyl 4-aminobenzoate
CC(C)N=C=NC(C)C
DIC
→
C=CCOC(=O)c1ccc(NC(=O)C(CC2(C)COC2)n2cc(OC)c(-c3cc(Cl)ccc3C#N)cc2=O)cc1
title compound
C=CCOC(=O)c1ccc(NC(=O)C(CC2(C)COC2)n2cc(OC)c(-c3cc(Cl)ccc3C#N)cc2=O)cc1
Allyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)propanoyl}amino)benzoate

Reactantes

CC#N.O
acetonitrile water
COc1cn(C(CC2(C)COC2)C(=O)O)c(=O)cc1-c1cc(Cl)ccc1C#N
2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)propanoic acid
C=CCOC(=O)c1ccc(N)cc1
allyl 4-aminobenzoate
CC(C)N=C=NC(C)C
DIC

Reactivos

Ninguno

Disolventes

CN(C)C=O
dimethylformamide

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

115 mg (285 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)propanoic acid (racemate), 51 mg (285 μmol) of allyl 4-aminobenzoate, 40.6 mg (285 μmol) of Oxima and 45 μl (0.29 mmol) of DIC in 2 ml of dimethylformamide were reacted according to General Method 5B. Preparative HPLC (acetonitrile/water gradient) gave the title compound. Yield: 25 mg (16% of theory)

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09434690B2uspto-grants-2016_09