Methylhydrazine → HCID 86291998, compound

HRID 873904Notes

Reaction equation

HRID 873904 reaction equation
[C:1]([C:4]1[CH:5]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:6]([C:11]2[CH:12]=[C:13]([CH3:19])[C:14](=[O:18])[N:15]([CH3:17])[CH:16]=2)[C:7](=[O:10])[C:8]=1O)(=O)[CH3:2].[CH3:27][NH:28][NH2:29]>C1(C)C=CC=CC=1.CCO.CCOCC>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH:5]2[C:4]3[C:1]([CH3:2])=[N:29][N:28]([CH3:27])[C:8]=3[C:7](=[O:10])[N:6]2[C:11]2[CH:12]=[C:13]([CH3:19])[C:14](=[O:18])[N:15]([CH3:17])[CH:16]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 6061MethylhydrazineHCID 117702570HCID 117702570, compound

Product 1

HCID 86291998HCID 86291998, compoundYield 37.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 5-(3-acetyl-2-(4-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-1,3-dimethylpyridin-2(1H)-one (Step 57.1) (500 mg, 1.341 mmol) in toluene (5 mL) and EtOH (5 mL) was added methyl hydrazine (0.353 mL, 6.71 mmol) and the reaction mixture was heated up and stirred at 110° C. for 18 hr. The reaction was concentrated under reduced pressure. The resulting mixture was diluted with AcOH (10 ml), heated up and stirred at 100° C. for 1 hr, concentrated under reduced pressure and quenched with a saturated aqueous NaHCO3 solution. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with EtOAc. Trituration in Et2O afforded the title product (191 mg, 0.499 mmol, 37% yield) as white solid. tR: 3.83 min (HPLC 1); tR: 0.91 min (LC-MS 2); ESI-MS: 383 [M+H]+ (LC-MS 2); Rf=0.09 (EtOAc); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.83-1.97 (m, 6H) 3.33 (s, 3H) 3.89 (s, 3H) 6.04 (s, 1H) 7.24 (d, J=8.2 Hz, 2H) 7.30-7.37 (m, 3H) 7.69 (d, J=2.7, Hz, 1H).

Workup

  1. temperaturethe reaction mixture was heated up
  2. concentrationThe reaction was concentrated under reduced pressure
  3. additionThe resulting mixture was diluted with AcOH (10 ml)
  4. temperatureheated up
  5. stirringstirred at 100° C. for 1 hr
  6. concentrationconcentrated under reduced pressure
  7. customquenched with a saturated aqueous NaHCO3 solution
  8. extractionThe aqueous layer was extracted with CH2Cl2
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. customevaporated under reduced pressure
  11. customThe crude product was purified by silica gel column chromatography
  12. washeluting with EtOAc

Sources & evidence

ORD record
ord-f1c7f76652954bb6b72a96350891b69d
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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