Formaldehyde → HCID 54691713, compound

HRID 2214522Notes

Reaction equation

COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.N[CH:24]([CH2:28][CH3:29])[C:25]([OH:27])=[O:26].[Cl:30][C:31]1[CH:32]=[C:33]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:34][N:35]([CH3:46])[C:36]([C:38]1[CH2:39][N:40](C)[C:41](=[O:44])[C:42]=1[OH:43])=[O:37]>>[Cl:30][C:31]1[CH:32]=[C:33]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:34][N:35]([CH3:46])[C:36]([C:38]1[CH2:39][N:40]([CH2:29][CH2:28][CH2:24][C:25]([OH:27])=[O:26])[C:41](=[O:44])[C:42]=1[OH:43])=[O:37]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 6657Alpha-Aminobutyric Acid

HCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamide

HCID 69655739HCID 69655739, compound2×

Product 1

HCID 54691713HCID 54691713, compoundYield 21%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and -aminobutyric acid 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 (42.1 mg, 21% yield). 1H NMR (300 MHz, CDCl3) δ: 7.42 (d, 1H, J=8.05), 7.36 (s, 1H), 7.11 (dd, 1H, J=8.05, J=1.10), 4.60 (s, 2H), 4.21 (s, 2H), 3.58 (t, 2H, J=6.22), 3.03 (s, 3H), 2.40 (t, 2H, J=6.95), 1.96 (t, 2H, J=6.59). HRMS (M−H) calcd for C17H17N2Cl2O5: 399.0514. found: 399.0509.

Workup

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-5a31fda6b8c548fb8ff53c97eaf95f07
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

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