Potassium Carbonate → HCID 24946490, compound

HRID 1011246Notes

Reaction equation

HRID 1011246 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:32][O:33][C:34]1[CH:39]=[C:38](B(O)O)[CH:37]=[CH:36][N:35]=1.O1CCOCC1>O>[CH2:24]([N:21]1[CH2:22][CH2:23][N:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:5]3[C:6]4[N:7]([N:8]=[CH:9][N:10]=4)[C:2]([C:38]4[CH:37]=[CH:36][N:35]=[C:34]([O:33][CH3:32])[CH:39]=4)=[CH:3][CH:4]=3)=[CH:13][CH:14]=2)[CH2:19][CH2:20]1)[CH3:25]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 57664345HCID 57664345, compound

Product 1

HCID 24946490HCID 24946490, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
107.5 °C

Procedure

To a reaction vial (40 mL), is added 5-chloro-N-(4-(4-ethylpiperazin-1-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (110 mg, 0.3 mmol), potassium carbonate (207 mg, 1.5 mmol, 5 eq.), 2-methoxypyridin-4-ylboronic acid (70 mg, 0.45 mmol, 1.5 eq), PddppfCl2 (44 mg, 20%), dioxane (4.0 mL) and water (1.0 mL). The reaction mixture is degassed and filled with argon. The reaction is heated at 105-110° C. for 20 h. After cooling to rt, ethyl acetate (10 mL) is added to each reaction vial. The organic phase is filtered through a pat of celite and then is evaporated to give a residue that is purified by silica gel column chromatography (1-3% 2N NH3 in MeOH/DCM) to give the title compound as a light yellow solid (90 mg, yield, 69.8%). 1H NMR (300 MHz, DMSO-d6): δ 8.75 (s, 1H), 8.56 (s, 1H), 8.26 (d, J=6.0 Hz, 1H), 7.60 (d, J=4.8 Hz), 7.58 (s, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.25 (d, J=9.0 Hz, 2H), 6.96 (d, J=9.0 Hz, 2H), 6.93 (d, J=8.4 Hz, 1H), 3.91 (s, 3H), 3.12 (m, 4H), 2.50 (m, 4H), 2.36 (q, J=6.9, 2H), 1.04 (t, J=6.9 Hz, 3H); LCMS-ESI (m/z): calcd for C24H27N7O, 429; [M+H]+ found, 430.

Workup

  1. customThe reaction mixture is degassed
  2. additionfilled with argon
  3. temperatureAfter cooling to rt
  4. additionethyl acetate (10 mL) is added to each reaction vial
  5. filtrationThe organic phase is filtered through a pat of celite
  6. customis evaporated
  7. customto give a residue that
  8. customis purified by silica gel column chromatography (1-3% 2N NH3 in MeOH/DCM)

Sources & evidence

ORD record
ord-7e24ae39750549d4a6dfedd5dbae5498
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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