Ethanol → HCID 178437980, compound

HRID 874004Notes

Reaction equation

HRID 874004 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12]([C:13](=O)[CH2:14][CH3:15])=[C:11](O)[C:10](=[O:18])[N:9]2[C:19]2[CH:20]=[C:21]([CH3:27])[C:22](=[O:26])[N:23]([CH3:25])[CH:24]=2)=[CH:4][CH:3]=1.O.[NH2:29][NH2:30].C(O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:12]3[C:13]([CH2:14][CH3:15])=[N:30][NH:29][C:11]=3[C:10](=[O:18])[N:9]2[C:19]2[CH:20]=[C:21]([CH3:27])[C:22](=[O:26])[N:23]([CH3:25])[CH:24]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 1177027685-(2-(4-chlorophenyl)-4-hydroxy-5-oxo-3-propionyl-2,5-dihydro-1H-pyrrol-1-yl)-1,3-dimethylpyridin-2(1H)-one

Product 1

HCID 178437980HCID 178437980, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-(2-(4-chlorophenyl)-4-hydroxy-5-oxo-3-propionyl-2,5-dihydro-1H-pyrrol-1-yl)-1,3-dimethylpyridin-2(1H)-one (Step 147.1) (1.5 g, 3.88 mmol), hydrazine monohydrate (0.942 mL, 19.39 mmol), ethanol (8 mL) and toluene (8 mL) was stirred for 18 h at reflux. The reaction mixture was concentrated, diluted with acetic acid (50 mL), stirred for 1 h at reflux, diluted with CH2Cl2/saturated aqueous solution of NaHCO3, and extracted twice with CH2Cl2. The combine organic extracts were washed with water and brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH 7.5%) and subsequent trituration of the resulting product in diethyl ether to afford 961 mg of the title compound as a yellow solid. tR: 0.82 min (LC-MS 2); ESI-MS: 383.1 [M+H]+ (LC-MS 2); Rf=0.19 (NH3 1%/CH2Cl2/MeOH 5%); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.90 (t, J=7.64 Hz, 3H) 1.94 (s, 3H) 2.35-2.47 (m, 2H) 3.38 (s, 3H) 6.15 (s, 1H) 7.25 (d, J=8.44 Hz, 2H) 7.31-7.51 (m, 3H) 7.73 (d, J=2.69 Hz, 1H) 13.41 (br. s., 1H).

Workup

  1. temperatureat reflux
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with acetic acid (50 mL)
  4. stirringstirred for 1 h
  5. temperatureat reflux
  6. additiondiluted with CH2Cl2/saturated aqueous solution of NaHCO3
  7. extractionextracted twice with CH2Cl2
  8. washThe combine organic extracts were washed with water and brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (CH2Cl2/MeOH 7.5%) and subsequent trituration of the resulting product in diethyl ether

Sources & evidence

ORD record
ord-7ee5641e3abd4f9f9c0617ebd869e40e
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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