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

HRID 2214507Notes

Reaction equation

HRID 2214507 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(F)=CC=1)C.C=O.[C:22]1([CH2:28][CH2:29][CH2:30][NH2:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[F:32][C:33]1[CH:51]=[CH:50][C:36]([CH2:37][N:38]([CH3:49])[C:39]([C:41]2[CH2:42]N(C)[C:44](=[O:47])[C:45]=2[OH:46])=[O:40])=[CH:35][CH:34]=1>>[F:32][C:33]1[CH:51]=[CH:50][C:36]([CH2:37][N:38]([CH3:49])[C:39]([C:41]2[CH2:42][N:31]([CH2:30][CH2:29][CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:44](=[O:47])[C:45]=2[OH:46])=[O:40])=[CH:35][CH:34]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 162593-PhenylpropylamineHCID 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 54698191N-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-1-(3-phenylpropyl)-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 3-phenyl-propylamine as described in the preparation of Compound 1. 1H NMR (500 MHz, CDCl3) δ: 1.93 (p, 2, J=7), 2.64 (t, 2, J=7), 2.99 (s, 3), 3.53 (t, 2, J=2), 4.10 (s, 2), 4.60 (s, 2), 7.02–7.28 (overlapping m, 9). 13C (125 MHz, CDCl3) δ: 29.77, 33.05, 34.56, 42.81, 48.79, 51.47, 109.25, 115.66, 115.83, 126.14, 128.30, 128.49, 129.34, 129.40, 132.16, 132.79, 140.88, 152.46, 161.39, 163.34, 165.02, 166.08.

Sources & evidence

ORD record
ord-0a4cd17cf79948e1866661df3405e659
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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