HCID 66599464, compound → HCID 66605740, compound

HRID 2410855Notes

Reaction equation

HRID 2410855 reaction equation
C([N:8]1[C:16]2[CH:15]=[C:14]([O:17][CH3:18])[CH:13]=[CH:12][C:11]=2[C:10]2[N:19]=[C:20]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[C:9]1=2)C1C=CC=CC=1>C(O)(C(F)(F)F)=O.FC(F)(F)S(O)(=O)=O>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]2[C:10]3[N:19]=[C:20]([N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[C:9]=3[NH:8][C:16]=2[CH:15]=1

Participants

4

Reactant 1

HCID 66599464HCID 66599464, compound

Product 1

HCID 66605740HCID 66605740, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 62406Trifluoromethanesulfonic acidCatalyst2×HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl 5-benzyl-7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (51 mg, 0.12 mmol) in TFA (2 mL) and two drops of trifluoromethanesulfonic acid was heated at reflux for 30 min. Another two drops of trifluoromethanesulfonic acid was added and heating continued for another 40 min. Preparative HPLC (100×30 mm Luna C18 column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile; gradient of 15 to 100% B over 20 min at 42 mL/min) followed by removal of the solvents afforded methyl 7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (15 mg, 0.044 mmol, 37% yield). MS (ESI) m/z 340.2 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.02 (1H, br. s.), 8.09 (1H, d, J=8.85 Hz), 7.22 (1H, s), 6.89 (1H, s), 6.85 (1H, d, J=8.55 Hz), 4.02 (3H, s), 3.90 (3H, s), 3.53-3.64 (4H, m), 1.69-1.80 (4H, m), 1.56-1.67 (2H, m).

Workup

  1. temperatureat reflux for 30 min
  2. temperatureheating
  3. customPreparative HPLC (100×30 mm Luna C18 column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile; gradient of 15 to 100% B over 20 min at 42 mL/min) followed by removal of the solvents

Sources & evidence

ORD record
ord-8b4b0be6ba77434192cf682a6c96572a
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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