Hydrazine hydrate (1:1) → HCID 57474467, compound

HRID 2043530Notes

Reaction equation

HRID 2043530 reaction equation
[F:1][CH:2]1[C:7]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=3)[NH:10][CH:9]=2)=[CH:6][CH2:5][N:4]([CH3:20])[CH2:3]1.O.NN>CO.[Ni]>[F:1][CH:2]1[C:7]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[NH:10][CH:9]=2)=[CH:6][CH2:5][N:4]([CH3:20])[CH2:3]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57474466HCID 57474466, compound

Product 1

HCID 57474467HCID 57474467, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of compound 132 (0.175 g, 0.635 mmol) in dry methanol (5 mL) was treated with hydrazine hydrate (0.198 mL, 6.357 mmol) followed by Ra—Ni (˜0.05 g) at room temperature. The reaction was placed in a pre-heated oil bath and refluxed for 2 min. The reaction was brought to room temperature, filtered through celite bed, washed with methanol (3×10 mL). The combined methanol layer was evaporated and crude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95) to obtain compound 133 (0.07 g, 45%) as a solid. mp 176-178° C.; 1H NMR (DMSO-d6) δ 2.30 (s, 3H), 2.40-2.56 (m, 1H), 2.73-2.83 (m, 1H), 2.99-3.08 (m, 1H), 3.30-3.42 (m, 1H), 4.51 (s, 2H), 5.37 (d, 1H, J=48.9 Hz), 6.22-6.26 (m, 1H), 6.51 (dd, 1H, J=1.8, 8.5 Hz), 6.97 (d, 1H, J=1.8 Hz), 7.08 (d, 1H, J=8.4 Hz), 7.27 (t, 1H, J=1.8 Hz), 10.72 (s, 1H); ESI-MS m/z (%): 246 (MH+, 12), 203 (100).

Workup

  1. customThe reaction was placed in a pre-heated oil bath
  2. temperaturerefluxed for 2 min
  3. customwas brought to room temperature
  4. filtrationfiltered through celite bed
  5. washwashed with methanol (3×10 mL)
  6. customThe combined methanol layer was evaporated
  7. customcrude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-dc73e3526a3e422499a7de9d355d38bc
Source dataset
uspto-grants-2013_11
Patent number
US08586620B2

Reaction notes

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