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

HRID 2214499Notes

Reaction equation

HRID 2214499 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(F)=CC=1)C.C=O.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH2:31])=[CH:25][CH:24]=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][C:26]3[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=3)[C:44](=[O:47])[C:45]=2[OH:46])=[O:40])=[CH:35][CH:34]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 674302-(4-Chlorophenyl)ethylamineHCID 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 546981831-[2-(4-chlorophenyl)ethyl]-N-[(4-fluorophenyl)methyl]-4-hydroxy-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 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.

Sources & evidence

ORD record
ord-8cf1ec89156347afa06bcc94c6fea0d1
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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