HCID 59004598, compound → HCID 59004626, compound

HRID 1668469Notes

Reaction equation

HRID 1668469 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[CH:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=1)[CH:8]=[CH:7]2)([O-])=O>CO.[Ni]>[NH2:19][C:16]1[N:17]=[CH:18][C:13]([N:9]2[C:10]3[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 59004598HCID 59004598, compound

Product 1

HCID 59004626HCID 59004626, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of compound 75 (200 mg, 0.79 mmol) in methanol (10 mL) was added to Raney Nickel (slurry in H2O, 50 mg) in a round bottom flask. The suspension was heated at reflux for 10 minutes then filtered through a pad of celite. The celite pad washed with methanol (20 mL). The filtrate was concentrated and the residue was subjected to silica gel chromatography (CH2Cl2 to MeOH:CH2Cl2, 1:9) to give compound 76 (140 mg, 79.1%) as an off-white solid. 1H NMR (DMSO-d6) δ 8.01 (d, J=2.7 Hz, 1H), 7.51 (dd, J=2.9, 6.1 Hz, 1H), 7.27 (d, J=3.0 Hz, 1H), 7.04 (d, J=8.6 Hz, 1H), 6.73 (d, J=2.1 Hz, 1H), 6.59 (s, 1H), 6.56 (s, 1H), 6.55 (dd, J=2.1, 6.8 Hz, 1H), 6.33 (d, J=3.0 Hz, 1H), 6.10 (brs, 2H), 4.61 (brs, 2H); ESI-MS (m/z, %): 225 (M+1, 100%).

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 10 minutes
  3. filtrationthen filtered through a pad of celite
  4. washThe celite pad washed with methanol (20 mL)
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0b41ff3aa98046d0968696b06246b62a
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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