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

HRID 2214514Notes

Reaction equation

HRID 2214514 reaction equation
COC(=O)C(O)=C[C:6](=O)[N:7](CC1C=CC(Cl)=C(Cl)C=1)[CH3:8].C=O.CC(N)CN.[Cl:28][C:29]1[CH:30]=[C:31]([CH:45]=[CH:46][C:47]=1[Cl:48])[CH2:32][N:33]([CH3:44])[C:34]([C:36]1[CH2:37][N:38]([CH3:43])[C:39](=[O:42])[C:40]=1[OH:41])=[O:35]>>[Cl:28][C:29]1[CH:30]=[C:31]([CH:45]=[CH:46][C:47]=1[Cl:48])[CH2:32][N:33]([CH3:44])[C:34]([C:36]1[CH2:37][N:38]([CH2:43][CH2:6][NH:7][CH3:8])[C:39](=[O:42])[C:40]=1[OH:41])=[O:35]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6567PropylenediamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 54698194N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-1-[2-(methylamino)ethyl]-5-oxo-2H-pyrrole-3-carboxamideYield 4%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and methyl-ethane-1,2-diamine as described in the preparation of Compound 12. The title compound was triturated with EtOAc to give a white solid (7.8 mg, 4% yield). 1H NMR (300 MHz, CDCl3) δ: 9.14, (bs, 1H), 7.40, (d, 1H, J=8.05), 7.34 (s, 1H), 7.11 (dd, 1H, J=8.05, J=1.10), 4.58, (s, 2H), 4.34, (s, 2H), 3.94 (m, 2H), 3.25 (m, 2H), 3.03 (s, 3H), 2.78 (s, 3H). HRMS (M+H) calcd for C16H19N3Cl2O3: 372.0881. found: 372.0886.

Workup

  1. customThe title compound was triturated with EtOAc

Sources & evidence

ORD record
ord-82f0cb2e977a4a569371f52df5ea9c0d
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

Loading…