HCID 54575307, compound → HCID 54575426, compound

HRID 2096276Notes

Reaction equation

HRID 2096276 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][CH:29]=1)[CH2:7][C:8]1[N:13]2[CH:14]=[C:15]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[CH:16]=[C:12]2[C:11](=[O:26])[NH:10][CH:9]=1)([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][CH:29]=1)[CH2:7][C:8]1[N:13]2[CH:14]=[C:15]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[CH:16]=[C:12]2[C:11](=[O:26])[NH:10][CH:9]=1

Participants

4

Reactant 1

HCID 54575307HCID 54575307, compound

Product 1

HCID 54575426HCID 54575426, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of EXAMPLE 14 (180 mg, 0.47 mmol) in methanol (20 ml) was added Raney nickel (20 mg). The mixture was stirred at room temperature under hydrogen overnight. Methanol (100 ml) was added and the mixture was heated until all solid material went into solution. The Raney nickel was filtered off, and the filtrate was concentrated to afford the title compound. MS (DCI/NH3) m/z 356 (M+H)+; 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 4.04 (s, 2H), 6.44 (d, J=5.42 Hz, 1H), 6.64 (d, J=7.46 Hz, 1H), 6.74 (s, 1H), 6.86 (d, J=7.46 Hz, 1H), 7.07-7.21 (m, 2H), 7.27 (s, 1H), 7.60 (s, 1H), 7.81 (d, J=2.03 Hz, 1H), 8.12 (d, J=7.80 Hz, 1H), 8.24 (d, J=3.73 Hz, 1H), 10.50 (d, J=5.42 Hz, 1H), 11.73 (s, 1H).

Workup

  1. temperaturethe mixture was heated until all solid material
  2. filtrationThe Raney nickel was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6d77eeef09e948f3836dbb57dfb55cce
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

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