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

Participants

Role	Name	HCID	Charge
Reactant	Formaldehyde	HCID 712	—
Reactant	Thiopheneethanamine	HCID 116521	—
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	N-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-1-[2-(2-thienyl)ethyl]-2H-pyrrole-3-carboxamide	HCID 54698185	—

Reaction Steps

3-[(4-Fluoro-benzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 1-D) was treated with paraformaldehyde and 2-thiophen-2-yl-ethylamine as described in the preparation of Compound 1. HRMS (M−H) calcd for C19H18FN2O3S: 373.1022. found: 373.1029. 1H NMR (500 MHz, CDCl3) δ: 2.95 (s, 3), 3.14 (t, 2, J=7), 3.76 (t, 2, J=7), 3.97 (s, 2), 4.57 (s, 2), 6.81–7.21 (overlapping m, 7). 13C NMR (125 MHz, CDCl3) δ: 28.76, 34.49, 44.93, 49.46, 51.47, 109.48, 115.65, 115.82, 124.20, 125.59, 127.15, 129.28, 129.34, 132.12, 132.14, 140.34, 152.72, 161.37, 163.33, 164.94, 166.11.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07109186B2
Source dataset	uspto-grants-2006_09
ORD ID	ord-72895f1cfa7e414a9268c7eae3a9cafa
Source note	uspto-grants-2006_09