Formaldehyde → 2-[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]acetic acid

HRID 2214519Notes

Reaction equation

COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.[NH2:23][CH2:24][C:25]([OH:27])=[O:26].[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(C)[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:23]([CH2:24][C:25]([OH:27])=[O:26])[C:39](=[O:42])[C:40]=1[OH:41])=[O:35]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 750Glycine

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

HCID 69655739HCID 69655739, compound2×

Product 1

HCID 546917302-[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]acetic acid

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and glycine as described in the preparation of Compound 12. The title compound was isolated as a white solid (80 mg, 43% yield). Mp=178–180° C. 1H NMR (300 MHz, DMSO) δ: 12.97 (bs, 1H), 11.07 (s, 1H), 7.62 (d, 1H, J=8.41), 7.53 (s, 1H), 7.25 (d, 1H, J=6.95), 4.59 (s, 2H), 4.15 (s, 2H), 4.10 (s, 2H), 2.98 (s, 3H). HRMS (M−H) calcd for C15H13N2Cl2O5: 371.0201. found: 371.0216.

Sources & evidence

ORD record: ord-e48b4a2913834277a16a11ca66720e2d
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

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