Formaldehyde → HCID 131725944, compound

HRID 2214526Notes

Reaction equation

HRID 2214526 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.[CH3:23][N:24]1[C:28]([CH2:29][C@H:30]([NH:34][C:35]([CH2:37][CH2:38]N)=[O:36])[C:31]([OH:33])=[O:32])=[CH:27][N:26]=[CH:25]1.[N+]([O-])(O)=O.[Cl:44][C:45]1[CH:46]=[C:47]([CH:61]=[CH:62][C:63]=1[Cl:64])[CH2:48][N:49]([CH3:60])[C:50]([C:52]1[CH2:53][N:54](C)[C:55](=[O:58])[C:56]=1[OH:57])=[O:51]>>[Cl:44][C:45]1[CH:46]=[C:47]([CH:61]=[CH:62][C:63]=1[Cl:64])[CH2:48][N:49]([CH3:60])[C:50]([C:52]1[CH2:53][N:54]([CH:29]([C:28]2[N:24]([CH3:23])[CH:25]=[N:26][CH:27]=2)[CH:30]([NH:34][C:35](=[O:36])[CH2:37][CH3:38])[C:31]([OH:33])=[O:32])[C:55](=[O:58])[C:56]=1[OH:57])=[O:51]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 112071Anserine nitrate (1:1)HCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 131725944HCID 131725944, compoundYield 1%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and L-anserine nitrate 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 solid (3.3 mg, 1% yield). 1H NMR (500 MHz, CDCl3) δ: 8.56 (s, 1H), 7.36 (d, 1H, J=8.24) 7.29 (m, 1H), 7.20 (s, 1H), 7.04 (m, 1H), 4.69 (m, 1H), 4.52 (s, 2H), 4.05 (s, 2H), 3.76 (s, 3H), 3.65 (t, 2H, J=5.80), 3.14 (m, 2H), 2.94 (s, 2H), 2.51 (m, 2H). HRMS (M+H) calcd for C23H26N5Cl2O6: 538.1260. found: 538.1280.

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-d6922ffbab464a84b4ff8c0d036230f6
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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