N-(6-Methoxypyridin-3-YL)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-YL)-9H-purin-6-YL)quinolin-2-amine → HCID 178492146, compound

HRID 1811911Notes

Reaction equation

HRID 1811911 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]([C:20]3[N:28]=[C:27]([CH3:29])[N:26]=[C:25]4[C:21]=3[N:22]=[CH:23][N:24]4C3CCCCO3)=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:5][CH:4]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]([C:20]3[N:28]=[C:27]([CH3:29])[N:26]=[C:25]4[C:21]=3[N:22]=[CH:23][NH:24]4)=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 66600625N-(6-Methoxypyridin-3-YL)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-YL)-9H-purin-6-YL)quinolin-2-amine

Product 1

HCID 178492146HCID 178492146, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(6-methoxypyridin-3-yl)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)quinolin-2-amine (21 mg, 0.045 mmol) in DCM (1 mL) and TFA (1 mL) was stirred at room temperature for 30 min. The solvents were removed under vacuum and the residue was dissolved in DCM, washed with saturated aqueous sodium bicarbonate (2×), water, and brine. The organic layer was dried over Na2SO4. The crude material was adsorbed onto a plug of silica gel and purified by silica gel chromatography (1 to 4% MeOH/CH2Cl2). The title compound was obtained as a yellow solid. m/z (ESI, +ve ion) 384 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 13.71 (s, 1H); 12.73 (s, 1H); 10.24 (s, 1H); 8.86 (s, 1H); 8.71 (s, 1H); 8.40 (d, J=7.0 Hz, 1H); 7.92 (d, J=7.8 Hz, 1H); 7.71 (br. s., 2H); 7.37 (br. s., 1H); 6.92 (d, J=8.6 Hz, 1H); 3.88 (s, 3H); 2.91 (s, 3H).

Workup

  1. customThe solvents were removed under vacuum
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with saturated aqueous sodium bicarbonate (2×), water, and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. custompurified by silica gel chromatography (1 to 4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f1d0d99178ef440f88781416dffd7c64
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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