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

Participants

Role	Name	HCID	Charge
Reactant	Formaldehyde	HCID 712	—
Reactant	Isopropylamine	HCID 6363	—
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-1-isopropyl-N-methyl-5-oxo-2H-pyrrole-3-carboxamide	HCID 54698192	—

Reaction Steps

3-[(4-Fluoro-benzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (compound 1-D) was treated with paraformaldehyde and isopropylamine as described in the preparation of Compound 1. 1H NMR (500 MHz, CDCl3) δ: 1.23 (d, 6, J=7), 3.02 (s, 3), 4.10 (s, 2), 4.45 (heptet, 1, J=7), 4.62 (s, 2), 7.03 (m, 2), 7.24 (m, 2). 13C NMR (125 MHz, CDCl3) δ: 20.61, 34.72, 44.09, 44.34, 110.21, 115.57, 115.75, 129.43, 129.50, 132.28, 132.30, 149.92, 161.35, 163.31, 164.76, 165.80.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07109186B2
Source dataset	uspto-grants-2006_09
ORD ID	ord-36d53c0bc57441618055f568d8ebd320
Source note	uspto-grants-2006_09