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

HRID 2214508Notes

Reaction equation

HRID 2214508 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(F)=CC=1)C.C=O.[CH:22]([NH2:25])([CH3:24])[CH3:23].[F:26][C:27]1[CH:45]=[CH:44][C:30]([CH2:31][N:32]([CH3:43])[C:33]([C:35]2[CH2:36]N(C)[C:38](=[O:41])[C:39]=2[OH:40])=[O:34])=[CH:29][CH:28]=1>>[F:26][C:27]1[CH:45]=[CH:44][C:30]([CH2:31][N:32]([CH3:43])[C:33]([C:35]2[CH2:36][N:25]([CH:22]([CH3:24])[CH3:23])[C:38](=[O:41])[C:39]=2[OH:40])=[O:34])=[CH:29][CH:28]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6363IsopropylamineHCID 54698182N-[(4-fluorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 696556793-[(4-Fluoro-benzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester

Product 1

HCID 54698192N-[(4-fluorophenyl)methyl]-4-hydroxy-1-isopropyl-N-methyl-5-oxo-2H-pyrrole-3-carboxamide

Procedure

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.

Sources & evidence

ORD record
ord-36d53c0bc57441618055f568d8ebd320
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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