Hydrazine → HCID 136148569, compound

HRID 30975Notes

Reaction equation

HRID 30975 reaction equation
[OH:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[N:6][N:5]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:4](=[O:16])[C:3]=1[C:17]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([N+:27]([O-])=O)=[CH:26][C:20]=2[S:19](=[O:31])(=[O:30])[N:18]=1.NN>CO.C1COCC1.[Ni]>[NH2:27][C:25]1[CH:24]=[CH:23][C:21]2[NH:22][C:17]([C:3]3[C:4](=[O:16])[N:5]([CH2:11][CH2:12][CH:13]([CH3:14])[CH3:15])[N:6]=[C:7]([CH:8]([CH3:10])[CH3:9])[C:2]=3[OH:1])=[N:18][S:19](=[O:30])(=[O:31])[C:20]=2[CH:26]=1

Participants

6

Reactant 2

HCID 9321HydrazineHCID 136148564HCID 136148564, compound

Product 1

HCID 136148569HCID 136148569, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5i (0.100 g, 0.22 mmol) in MeOH (5 mL) and THF (5 mL) was added Raney-Nickel (0.6 mL, 50% slurry in H2O) followed by anhydrous NH2NH2 (0.3 mL, 9.56 mmol). The reaction mixture was stirred 15 min at ambient temperature, filtered using a syringe filter with 0.2 μm PTFE membrane, and concentrated in vacuo. The crude mixture was purified by flash column chromatography using silica gel eluted with 0-3% MeOH/CH2Cl2 to give 5j (0.072 g, 77%) as a red solid. 1H NMR (400 MHz, D6-DMSO) δ 7.0 (br s, 1 H), 6.93 (s, 1 H), 6.79 (d, J=2.8 Hz, 1 H), 6.76 (d, J=2.4 Hz), 5.33 (br s, 2 H), 3.86 (t, J=6.8 Hz, 2 H), 3.22 (m, 1 H), 1.52 (m, 3 H), 1.08 (d, J=7.2 Hz, 6 H), 0.90 (d, J=6.4 Hz, 6 H). MS(ESI+) m/e 420 [M+H]+.

Workup

  1. filtrationfiltered
  2. filtrationfilter with 0.2 μm PTFE membrane
  3. concentrationconcentrated in vacuo
  4. customThe crude mixture was purified by flash column chromatography
  5. washeluted with 0-3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-2527ed3835854d1b958d13dd38ac9300
Source dataset
uspto-grants-2008_09
Patent number
US07425552B2

Reaction notes

Loading…