Hydrazine → HCID 58865803, compound

HRID 1354835Notes

Reaction equation

HRID 1354835 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]([NH:55][C:56](=[O:66])[C:57]4[CH:62]=[CH:61][C:60]([N+:63]([O-])=O)=[CH:59][CH:58]=4)[CH:29]=3)[N:24]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NN>CCOC(C)=O.CO.[Ni]>[NH2:63][C:60]1[CH:61]=[CH:62][C:57]([C:56]([NH:55][C:28]2[CH:29]=[C:30]3[C:25](=[CH:26][CH:27]=2)[N:24]=[C:23]([N:11]2[CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:14][C@@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)[C:32]([N:33]2[CH2:38][C@@H:37]([NH:39][C:40]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[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]2)=[N:31]3)=[O:66])=[CH:58][CH:59]=1

Participants

6

Reactant 2

HCID 9321HydrazineHCID 58865679HCID 58865679, compound

Product 1

HCID 58865803HCID 58865803, compoundYield 100.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

N-(2,3-bis-((3R,5S)-3,5-bis-(tert-Butoxycarbonylamino)-piperidin-1-yl)-quinoxalin-6-yl)-4-nitro-benzamide (251) (0.063 g, 0.068 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. The mixture was passed through a plug of silica gel and concentrated to give an orange 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 as an orange powder (0.061 g, 0.0684 mmol, 99% yield). LC-MS (ESI): (exact mass: 890.50) m/e=891.9 [M+1]+.

Workup

  1. customBubbling
  2. concentrationconcentrated
  3. customto give an orange 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-501595980a2640918b46b7aa9edf2433
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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