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

HRID 2214513Notes

Reaction equation

HRID 2214513 reaction equation
CO[C:3](=[O:20])[C:4]([OH:19])=[CH:5][C:6](=[O:18])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)[CH3:8].C=O.C1(N)CC1.ClC1C=C(C=CC=1Cl)CN(C)C([C:35]1C[N:37]([CH3:42])[C:38](=O)[C:39]=1O)=O>>[Cl:17][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[Cl:16])[CH2:9][N:7]([CH3:8])[C:6]([C:5]1[CH2:42][N:37]([CH:38]2[CH2:39][CH2:35]2)[C:3](=[O:20])[C:4]=1[OH:19])=[O:18]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 69828CyclopropylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 546981931-cyclopropyl-N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-2H-pyrrole-3-carboxamideYield 30%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and cyclopropylamine as described in the preparation of Compound 12. The title compound was extracted with EtOAc and the organic layer was washed with H2O, and dried over Na2SO4. After concentration, the resulting residue was triturated with EtOAc/Hexane (1:1) to give a white solid (52.7 mg, 30% yield). Mp=163–164° C. 1H NMR (300 MHz, CDCl3) δ: 9.97 (bs, 1H), 7.42, (d, 1H, J=8.42), 7.35 (s, 1H), 7.10 (dd, 1H, J=8.42, J=1.47), 4.60 (s, 2H), 4.09 (s, 2H), 3.02 (s, 3H), 2.81 (m, 1H), 0.86 (m, 4H). HRMS (M+H) calcd for C16H17N2Cl2O3: 355.0616. found: 355.0618.

Workup

  1. extractionThe title compound was extracted with EtOAc
  2. washthe organic layer was washed with H2O
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe resulting residue was triturated with EtOAc/Hexane (1:1)

Sources & evidence

ORD record
ord-c4d73387400e411294a19bd49d8c5678
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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