Trifluoromethanesulfonic acid → HCID 66825680, compound

HRID 1046507Notes

Reaction equation

HRID 1046507 reaction equation
COC1C=CC(C[N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[C:12]([NH:17][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:11]=3[C:10]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:9]2)=CC=1.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[O:24]([C:10]1[C:11]2[C:12]([NH:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[N:13][CH:14]=[CH:15][C:16]=2[NH:8][N:9]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 66825545HCID 66825545, compound

Product 1

HCID 66825680HCID 66825680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 1-(4-methoxybenzyl)-3-phenoxy-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[4,3-c]pyridin-4-amine from step 1 was added to methylene chloride (5 mL) and trifluoromethanesulfonic acid (0.5 mL), and the resulting mixture was stirred at room temperature for two hours. The mixture was concentrated under reduced pressure and the residue was purified by reverse phase HPLC to give 3-phenoxy-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[4,3-c]pyridin-4-amine: LC-MS (Method G): m/z=311.1; 1H NMR (400 MHz, DMSO): δ 12.43 (s, 1H), 7.73 (d, J=6.1, 1H), 7.42 (t, J=7.9, 2H), 7.26 (d, J=8.0, 2H), 7.19 (t, J=7.3, 1H), 6.60 (d, J=6.1, 1H), 5.43 (d, J=7.7, 1H), 4.19 (m, 1H), 3.79 (d, J=11.6, 2H, 1.83 (d, J=12.4, 2H), 1.43 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-395026feb0aa4c508a5a6f7f63e857a7
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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