Formaldehyde → 1-[2-(4-chlorophenyl)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	2-(4-Chlorophenyl)ethylamine	HCID 67430	—
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-chlorophenyl)ethyl]-N-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-2H-pyrrole-3-carboxamide	HCID 54698183	—

Reaction Steps

3-[(4-Fluoro-benzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 1-D) was treated with paraformaldehyde and 2-(4-chlorophenyl)-ethylamine as described in the preparation of Compound 1. HRMS (M−H) calcd for C21H19ClFN2O3; 401.1068. found: 401.1080. 1H NMR (500 MHz, CDCl3)δ: 2.90 (t, 2, j=7), 2.95 (s, 3), 3.72 (t, 2, J=7), 3.95 (s, 2), 4.57 (s, 2), 7.03–7.26 (overlapping m, 8). 13C NMR (125 MHz, CDCl3) δ: 33.92, 34.45, 44.42, 49.37, 51.46, 108.49, 118.91, 128.87, 129.22, 129.98, 131.99, 132.67, 136.60, 154.21, 161.42, 163.37, 164.51, 166.31.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07109186B2
Source dataset	uspto-grants-2006_09
ORD ID	ord-8cf1ec89156347afa06bcc94c6fea0d1
Source note	uspto-grants-2006_09