Hydrazine → HCID 58865622, compound

HRID 1354833Notes

Reaction equation

HRID 1354833 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][C@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][N:11]([C:23]2[C:32]([N:33]3[CH2:38][C@@H:37]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][C@@H:35]([NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:34]3)=[N:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([N+:55]([O-])=O)[CH:29]=3)[N:24]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NN>CCOC(C)=O.CO.[Ni]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][C@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][N:11]([C:23]2[C:32]([N:33]3[CH2:34][C@@H:35]([NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:36][C@@H:37]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:38]3)=[N:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([NH2:55])[CH:29]=3)[N:24]=2)[CH2:10]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 2

HCID 9321HydrazineHCID 58865534HCID 58865534, compound

Product 1

HCID 58865622HCID 58865622, compoundYield 88.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

2,3-Bis-((3R,5S)-3,5-bis-(tert-Butoxycarbonylamino)-piperidin-1-yl)-6-nitro-quinoxaline (3) (0.159 g, 0.198 mmol) was dissolved in a mixture of EtOAc (3 mL) and MeOH (3 mL). The solution was heated to 60° C. and Raney Nickel (0.25 mL, 50% slurry in water) and hydrazine (0.5 mL, anhydrous) were added. Bubbling was observed. The mixture continued to stir for 15 minutes at 60° C. TLC (Rf: 0.05 compared to Rf: 0.3 for compound 245 in 1:1 hexanes/EtOAc) indicated complete reduction at this point. The mixture was passed through a plug of silica gel and concentrated to give a white powder. The solid was dissolved in EtOAc (30 mL), washed with water (2×20 mL) and brine (2×20 mL) via extraction, dried over MgSO4 and concentrated to give the desired product (246) as a white powder (0.135 g, 0.175 mmol, 88.3% yield). LC-MS (ESI): (exact mass: 771.46) m/e=772.6 [M+1]+.

Workup

  1. customBubbling
  2. concentrationconcentrated
  3. customto give a white powder
  4. washwashed with water (2×20 mL) and brine (2×20 mL) via extraction
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d6b5fd5cc9444638829e29063a6883ca
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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