Hydrazine hydrate (1:1) → HCID 67960143, compound

HRID 1529357Notes

Reaction equation

HRID 1529357 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([N+:30]([O-])=O)[CH:28]=4)[N:23]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:22]=3)[CH:18]=[N:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>CO.[Ni]>[NH2:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[N:23]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:22]=[C:21]2[C:19]1[CH:18]=[N:17][CH:16]=[C:15]([N:12]2[CH2:13][CH2:14][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11]2)[N:20]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67959775HCID 67959775, compound

Product 1

HCID 67960143HCID 67960143, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 3-(6-(4-(tert-butoxycarbonylamino)piperidin-1-yl)pyrazin-2-yl)-5-nitro-1H-indole-1-carboxylate (200 mg, 0.37 mmol) in MeOH (2 mL) was added Raney Ni (30 mg) and then heated at 50° C. for 5 min. Hydrazine hydrate (0.2 mL) was added and the resulting mixture was stirred at the same temperature for another 10 min. The reaction mixture was cooled to RT and filtered off the Raney Ni through Celite. The filtrate was concentrated to obtain the title compound as a pale brown solid (160 mg, 85%). MS (ESI, pos. ion) m/z: 509.3 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered off the Raney Ni through Celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-62e1b21f9d664698bfa834abb214f06a
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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