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

HRID 2214515Notes

Reaction equation

HRID 2214515 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.[CH3:23][C:24]([CH3:28])([CH3:27])[CH2:25][NH2:26].[Cl:29][C:30]1[CH:31]=[C:32]([CH:46]=[CH:47][C:48]=1[Cl:49])[CH2:33][N:34]([CH3:45])[C:35]([C:37]1[CH2:38]N(C)[C:40](=[O:43])[C:41]=1[OH:42])=[O:36]>>[Cl:29][C:30]1[CH:31]=[C:32]([CH:46]=[CH:47][C:48]=1[Cl:49])[CH2:33][N:34]([CH3:45])[C:35]([C:37]1[CH2:38][N:26]([CH2:25][C:24]([CH3:28])([CH3:27])[CH3:23])[C:40](=[O:43])[C:41]=1[OH:42])=[O:36]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 79882NeopentylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 54698195N-[(3,4-dichlorophenyl)methyl]-1-(2,2-dimethylpropyl)-4-hydroxy-N-methyl-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 2,2-dimethyl-propylamine as described in the preparation of Compound 12. The resulting residue was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA) to yield the title compound as a white powder (7.9 mg, 4% yield). 1H NMR (500 MHz, DMSO) δ: 7.42 (d, 1H, J=8.24), 7.36 (s, 1H), 7.12 (d, 1H, J=8.24), 4.61 (s, 2H), 4.26 (s, 2H), 3.27 (s, 2H), 3.04 (s, 3H), 0.93 (s, 9H). HRMS (M+H) calcd for C18H23N2Cl2O3: 385.1085; found: 385.1079.

Workup

  1. customThe resulting residue was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-769641451b3843189a448fcbccaf19d8
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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