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

HRID 552964Notes

Reaction equation

HRID 552964 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-5c258ab754eb496e945fa29995141bf5
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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