Hydrazine hydrate (1:1) → HCID 59160549, compound

HRID 1958674Notes

Reaction equation

HRID 1958674 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=3)=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[N:15]4)[N:11]=2)=[CH:4][C:3]=1[N+:31]([O-])=O.O.NN>CO.[Ni]>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=3)=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[N:15]4)[N:11]=2)=[CH:4][C:3]=1[NH2:31]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59160541HCID 59160541, compound

Product 1

HCID 59160549HCID 59160549, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 6-(2-(4-fluoro-3-nitrobenzyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoxaline (49.6 mg, 0.113 mmol, prepared according to the method described in US 2008/0319012 A1) in MeOH (5 mL) were added Raney Ni (0.1 mg, 10% w/w) and hydrazine monohydrate (0.027 mL, 0.563 mmol) and the mixture was stirred at room temperature for overnight. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by MPLC (MeOH:CH2Cl2=1:50 (v/v)) and on NH silica gel (MeOH:CH2Cl2=1:100 (v/v)) to afford the title compound (37.8 mg, 82%). (300 MHz, CDCl3) δ 1.99 (4H, m), 2.54 (3H, s), 3.23 (4H, t), 4.31 (2H, s), 6.37 (1H, dd), 6364 (1H, d), 6.95 (1H, d), 7.23-7.43 (5H, m), 7.98 (1H, dd), 8.08-8.17 (3H, m), 8.91 (1H, dd), 10.40 (1H, bs) MS (ESI) m/z 446 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by MPLC (MeOH:CH2Cl2=1:50 (v/v)) and on NH silica gel (MeOH:CH2Cl2=1:100 (v/v))

Sources & evidence

ORD record
ord-f25f549b26a14bb0a2c412c1a1ab8b60
Source dataset
uspto-grants-2013_04
Patent number
US08410146B2

Reaction notes

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