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

HRID 2214512Notes

Reaction equation

HRID 2214512 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH2:10]=O.CO[C:14](=[O:31])[C:15]([OH:30])=[CH:16][C:17](=[O:29])[N:18]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=1)[CH3:19]>CC(O)=O>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[Cl:27])[CH2:20][N:18]([CH3:19])[C:17]([C:16]1[CH2:10][N:1]([CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)[C:14](=[O:31])[C:15]=1[OH:30])=[O:29]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4082852-MorpholinoethylamineHCID 69655739HCID 69655739, compound

Product 1

HCID 54691036N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-1-(2-morpholinoethyl)-5-oxo-2H-pyrrole-3-carboxamideYield 24%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 0.5 mL of AcOH at 60° C. was added N-(2-aminoethyl)morpholine (0.066 mL, 0.5 mmol) and paraformaldehyde (15 mg, 0.5 mmol). After stirring for 5 min, 3-[(3,4-dichloro-benzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (159 mg, 0.5 mmol) was added and the resulting mixture stirred at 60° C. for 2 h. The reaction mixture was cooled to room temperature and extracted with EtOAc. The remaining aqueous layer was extracted with CH2Cl2, and dried over Na2SO4. Concentration yielded 51.1 mg (24% yield) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3) δ: 10.52 (bs, 1H), 7.40 (d, 1H, J=10.61), 7.39 (s, 1H), 7.11 (dd, 1H, J=10.24, J=1.83), 4.60 (s, 2H), 4.23 (s, 2H), 3.64 (m, 6H), 3.01 (s, 3H), 2.63 (t, 2H, J=6.22), 2.54, (m, 4H), 2.05 (s, 3H). MS (M+H) calcd for C19H23N3O4Cl2: 427.1; found: 428.11.

Workup

  1. stirringthe resulting mixture stirred at 60° C. for 2 h
  2. extractionextracted with EtOAc
  3. extractionThe remaining aqueous layer was extracted with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-da6e70e3093d4138bc4eb4ab4603f562
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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