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

HRID 2214524Notes

Reaction equation

HRID 2214524 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.[NH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[Cl:32][C:33]1[CH:34]=[C:35]([CH:49]=[CH:50][C:51]=1[Cl:52])[CH2:36][N:37]([CH3:48])[C:38]([C:40]1[CH2:41]N(C)[C:43](=[O:46])[C:44]=1[OH:45])=[O:39]>>[Cl:32][C:33]1[CH:34]=[C:35]([CH:49]=[CH:50][C:51]=1[Cl:52])[CH2:36][N:37]([CH3:48])[C:38]([C:40]1[CH2:41][N:23]([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:43](=[O:46])[C:44]=1[OH:45])=[O:39]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 33944N-(2-Aminoethyl)piperidineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 54698201N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-1-[2-(1-piperidyl)ethyl]-2H-pyrrole-3-carboxamideYield 38%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and 1-(2-aminoethyl)piperidine as described in the preparation of Compound 12. The resulting residue was purified by trituration with CH2Cl2 to yield the title compound as a white solid (81.2 mg, 38% yield). Decomposition point=178–182° C. 1H NMR (300 MHz, DMSO) δ: 10.99 (s, 1H), 7.62 (d, 1H, J=8.25), 7.52 (d, 1H, J=1.46), 7.26 (d, 1H, J=7.68), 4.60 (s, 2H), 4.13 (s, 2H), 3.81 (t, 2H, J=5.85), 3.48 (d, 2H, J=11.34), 3.27 (d, 2H. J=4.76), 3.00 (s, 2H), 2.86 (m, 3H), 1.77 (m, 6H). HRMS (M+H) calcd for C20H26N3Cl2O3: 426.1351. found: 426.1346.

Workup

  1. customThe resulting residue was purified by trituration with CH2Cl2

Sources & evidence

ORD record
ord-078930b2291c46f89d80e34c5e18821a
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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