Sodium Carbonate → HCID 68078444, compound

HRID 1522395Notes

Reaction equation

HRID 1522395 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29](B(O)O)[CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CS(C)=O>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([C:29]2[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=2)[CH:3]=1)=[O:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 565974256-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Product 1

HCID 68078444HCID 68078444, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a 5-mL microwave vial were added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.187 mmol), 3-pyridinylboronic acid (29.9 mg, 0.243 mmol), DMSO (1.5 mL) and sodium carbonate (0.281 mL, 0.562 mmol), and the mixture was degassed with nitrogen for 10 min. Next was added bis(triphenylphosphine)palladium(II) chloride (10.51 mg, 0.015 mmol) and the vial was sealed. The reaction mixture was irradiated (microwave) at 140° C. overnight. The reaction mixture was filtered and the residue was washed with DMSO. The crude product in DMSO was purified using reverse-phase HPLC. The TFA salt of the product was neutralized using saturated NaHCO3, filtered, washed with water and dried under high vacuum to give 33 mg (42%) of product. LCMS E-S (M+H)=417.2 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (d, J=6.4 Hz, 6 H), 2.13 (s, 3 H), 2.23 (s, 3 H), 4.42 (d, J=4.29 Hz, 2 H), 5.26-5.43 (m, 1 H), 5.91 (s, 1 H), 7.62 (dd, J=7.3, 5.0 Hz, 1 H), 8.26 (s, 1 H), 8.43 (s, 1 H), 8.64 (d, J=7.8 Hz, 1 H), 8.70-8.79 (m, 1 H), 8.96 (br. s., 1 H), 9.46 (br. s., 1 H), 11.59 (br. s., 1 H).

Workup

  1. customthe mixture was degassed with nitrogen for 10 min
  2. customthe vial was sealed
  3. customThe reaction mixture was irradiated (microwave) at 140° C. overnight
  4. filtrationThe reaction mixture was filtered
  5. washthe residue was washed with DMSO
  6. customThe crude product in DMSO was purified
  7. filtrationfiltered
  8. washwashed with water
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-43d632c0ea0540f681dcad6c2a86fbcc
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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