Potassium Carbonate → HCID 24946129, compound

HRID 1011245Notes

Reaction equation

HRID 1011245 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][CH2:25][CH3:26])[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:33]([C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1)(=[O:35])[NH2:34].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:39]4[CH:40]=[CH:41][C:36]([C:33]([NH2:34])=[O:35])=[CH:37][CH:38]=4)=[CH:3][CH:4]=3)=[CH:13][CH:14]=2)[CH2:19][CH2:20]1)[CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27378114-Aminocarbonylphenylboronic acidHCID 57664375HCID 57664375, compound

Product 1

HCID 24946129HCID 24946129, compoundYield 42.2%

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-propylpiperazin-1-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (55 mg, 0.15 mmol), potassium carbonate (104 mg, 0.75 mmol, 5 eq.), 4-carbamoylphenylboronic acid (50 mg, 0.30 mmol, 2 eq), PddppfCl2 (20 mg, 15%), 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 was filtered through a pat of celite and then is evaporated to give a dry residue that was purified by preparatory HPLC to give the title compound, 28.9 mg, yield 42.2%; LCMS-ESI (m/z): calcd for C26H29N7O, 455; [M+H]+ found, 456.

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 was filtered through a pat of celite
  6. customis evaporated
  7. customto give a dry residue that
  8. customwas purified by preparatory HPLC

Sources & evidence

ORD record
ord-1751fa034b814cd1a72240a6e37fb267
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

Loading…