p-Toluenesulfonic acid → HCID 58213670, compound

HRID 340304Notes

Reaction equation

HRID 340304 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([C:16](O)([CH3:18])[CH3:17])=[CH:15][C:4]=2[N:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:17]=[C:16]([C:14]1[CH:13]=[CH:12][C:5]2=[C:6]3[C:11](=[C:2]([NH2:1])[N:3]=[C:4]2[CH:15]=1)[N:10]=[CH:9][CH:8]=[CH:7]3)[CH3:18]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66874757HCID 66874757, compound

Product 1

HCID 58213670HCID 58213670, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(5-aminobenzo[f][1,7]naphthyridin-8-yl)propan-2-ol (from the previous step) (1.0 eq.) and p-TsOH (2 eq.) in toluene (0.01 M) was stirred at 90° C. for 6 hours. The reaction was quenched by saturated NaHCO3 and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4 and concentrated en vacuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% MeOH/DCM to give 8-(prop-1-en-2-yl)benzo[f][1,7]naphthyridin-5-amine as a yellow solid.

Workup

  1. customThe reaction was quenched by saturated NaHCO3
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated en vacuo
  6. customto obtain a crude residue
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-1fe16387b18345eba25b98b3dd46e105
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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