HCID 18005067, compound → HCID 18005103, compound

HRID 1668466Notes

Reaction equation

HRID 1668466 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]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH:8]=[CH:7]2)([O-])=O>CO.[Ni]>[N:15]1[CH:16]=[CH: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]=1

Participants

4

Reactant 1

HCID 18005067HCID 18005067, compound

Product 1

HCID 18005103HCID 18005103, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of compound 72 (350 mg, 1.46 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, 5:95) to give compound 73 (300 mg, 98.4%) as a viscous oil. 1H NMR (DMSO-d6) δ 8.81 (d, J=2.6 Hz, 1H), 8.53-8.51 (m, 1H), 8.02-7.99 (m, 1H), 7.56-7.54 (m, 2H), 7.32 (d, J=8.7 Hz, 1H), 6.77 (d, J=1.9 Hz, 1H), 6.59 (dd, J=2.1, 6.7 Hz, 1H), 6.47 (d, J=3.4 Hz, 1H), 4.72 (brs, 2H); ESI-MS (m/z, %): 210 (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-64790d9ae84441d4bc699a400ae852ab
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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