4-Methoxybenzohydrazide → HCID 69003859, compound

HRID 2102302Notes

Reaction equation

HRID 2102302 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[N:15]=2)[C:12](OC)=[N:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][O:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([NH:36][NH2:37])=O)=[CH:32][CH:31]=1>CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]2[C:34]([C:33]3[CH:38]=[CH:39][C:30]([O:29][CH3:28])=[CH:31][CH:32]=3)=[N:36][N:37]=[C:12]2[CH:13]1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[N:15]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 767924-MethoxybenzohydrazideHCID 69004179HCID 69004179, compound

Product 1

HCID 69003859HCID 69003859, compoundYield 20.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-5-methoxy-3,6-dihydro-2H-pyrazine-1-carboxylic acid tert-butyl ester (284.6 mg, 0.70 mmol) and 4-methoxy-benzoic acid hydrazide (116.2 mg, 0.70 mmol) under argon in methanol (10 mL) were heated at reflux for 3 days. After cooling, the reaction mixture was diluted with ethyl acetate and then washed with water (3 times) and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel using 40-85% ethyl acetate in hexanes afforded the titled compound (72.5 mg, 20%). 1H NMR (CDCl3) δ (ppm): 8.07 (m, 1H), 7.96 (m, 1H), 7.64 (m, 2H), 7.47 (m, 2H), 7.05 (m, 2H), 6.04 (m, 1H), 4.11 (m, 2H), 3.89 (s, 3H), 3.86 (m, 2H), 3.55 (m, 1H), 3.31 (m, 1H), 1.28 (bs, 9H).

Workup

  1. temperatureat reflux for 3 days
  2. temperatureAfter cooling
  3. washwashed with water (3 times) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel using 40-85% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7b5f59ec01084399802a0c73b0303b05
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

Loading…