Formaldehyde → HCID 54704647, compound

HRID 2214530Notes

Reaction equation

HRID 2214530 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][NH2:32])[CH2:26][CH2:25]1.[Cl:33][C:34]1[CH:35]=[C:36]([CH:50]=[CH:51][C:52]=1[Cl:53])[CH2:37][N:38]([CH3:49])[C:39]([C:41]1[CH2:42]N(C)[C:44](=[O:47])[C:45]=1[OH:46])=[O:40]>>[Cl:33][C:34]1[CH:35]=[C:36]([CH:50]=[CH:51][C:52]=1[Cl:53])[CH2:37][N:38]([CH3:49])[C:39]([C:41]1[CH2:42][N:32]([CH2:31][CH2:30][N:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)[C:44](=[O:47])[C:45]=1[OH:46])=[O:40]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 702844-Methylpiperazine-1-ethylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 54704647HCID 54704647, compoundYield 12%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and 2-(4-methyl-piperazine-1-yl)-ethyl amine 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 an amber glass (27 mg, 12% yield). 1H NMR (300 MHz, DMSO) δ: 7.63 (d, 1H, J=8.42), 7.52 (s, 1H), 7.25 (d, 1H, J=7.31), 4.59 (s, 2H), 4.24 (m, 10H), 4.11 (s, 2H), 3.58 (s, 2H), 2.98 (s, 3H), 2.78 (s, 3H). HRMS (M−H) calcd for C20H25N4Cl2O3: 439.1303. found: 439.1311.

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-f454d731f8784a0180d216fbc2384e2a
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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