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

HRID 2214502Notes

Reaction equation

HRID 2214502 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(F)=CC=1)C.C=O.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][NH2:31].[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:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[F:22])[C:44](=[O:47])[C:45]=2[OH:46])=[O:40])=[CH:35][CH:34]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6433572-(2-Fluorophenyl)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 546981861-[2-(2-fluorophenyl)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-(2-fluoro-phenyl)-ethylamine as described in the preparation of Compound 1. HRMS (M+H) calcd for C21H21N2F2O3: 387.1520. found: 387.1525. 1H NMR (500 MHz, CDCl3) δ: 2.96 (overlapping m, 5), 3.75 (t, 2, J=7), 4.02 (s, 2), 4.58 (s, 2), 6.98–7.22 (overlapping m, 8). 13C NMR (125 MHz, CDCl3) δ: 28.13, 28.14, 34.55, 43.38, 49.34, 51.52, 109.53, 115.31, 115.48, 115.68, 115.85, 124.38, 124.41, 124.87, 124.99, 128.68, 128.75, 129.29, 129.35, 130.96, 130.99, 131.98, 132.01, 152.46, 160.26, 161.40, 162.21, 163.36, 165.04, 166.09.

Sources & evidence

ORD record
ord-0ff15b32affa4faa8e14ce5329f4268a
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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