Formaldehyde → 1-[2-(4-fluorophenyl)ethyl]-N-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-2H-pyrrole-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Formaldehyde	HCID 712	—
Reactant	p-Fluorophenethylamine	HCID 4653	—
Reactant	N-[(4-fluorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamide	HCID 54698182	—
Reactant	3-[(4-Fluoro-benzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester	HCID 69655679	—
Product	1-[2-(4-fluorophenyl)ethyl]-N-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-2H-pyrrole-3-carboxamide	HCID 54698190	—

Reaction Steps

3-[(4-Fluoro-benzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 1-D) was treated with paraformaldehyde and 2-(4-fluoro-phenyl)-ethylamine as described in the preparation of Compound 1. (HRMS (M−H) calcd for C21H19F2N2O3: 385.1364. found: 385.1377. 1H NMR (500 MHz, CDCl3) δ: 2.90 (t, 2, J=7), 2.95 (s, 3), 3.71 (t, 2, J=7), 3.95 (s, 2), 4.57 (s, 2), 6.95–7.26 (overlapping m, 8). 13C NMR (125 MHz, CDCl3) δ: 33.74, 34.48, 44.70, 49.41, 51.47, 108.82, 115.49, 115.66, 115.71, 115.77, 115.89, 129.22, 129.27, 130.04, 130.10, 131.97, 133.72, 153.60, 160.81, 161.42, 162.76, 163.38, 164.71, 166.21.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07109186B2
Source dataset	uspto-grants-2006_09
ORD ID	ord-ce21a97f357b4f37af888f7bd1a24f7a
Source note	uspto-grants-2006_09