Sodium Carbonate → HCID 86672647, compound

HRID 1616364Notes

Reaction equation

HRID 1616364 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([NH:21][CH:22]([CH3:24])[CH3:23])[N:20]=1)[C:5]([NH:7][CH2:8][C:9]1[C:10](=[O:17])[NH:11][C:12]([CH3:16])=[CH:13][C:14]=1[CH3:15])=[O:6].B(O)O.[C:28]([O-:31])([O-])=O.[Na+].[Na+].O1[CH2:39][CH2:38]OCC1.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][C:14]1[CH:13]=[C:12]([CH3:16])[NH:11][C:10](=[O:17])[C:9]=1[CH2:8][NH:7][C:5](=[O:6])[C:4]1[CH:18]=[C:19]([NH:21][CH:22]([CH3:24])[CH3:23])[N:20]=[C:2]([C:39]2[CH:38]=[CH:5][C:4]([CH:28]=[O:31])=[CH:3][CH:2]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 218864351,4-Dioxane--water (1/1)HCID 86672648HCID 86672648, compound

Product 1

HCID 86672647HCID 86672647, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(isopropylamino)isonicotinamide (0.58 g, 1.67 mmol), boronic acid (0.277 g, 1.84 mmol) in dioxane/water mixture (7 mL+3 mL), Na2CO3 (0.64 g, 6.037 mmol) was added and reaction mass purged for 15 min with argon. Then Pd(PPh3)4 (0.194 g, 0.168 mmol) was added and argon was purged again for 10 min. Reaction mass was heated at 100° C. for 3 h. On completion, reaction mass filtered through celite and celite bed washed with ethyl acetate. Combined filtrates were dried over Na2SO4 and solvent removed under reduced pressure to afford crude material which was purified by column over silica gel to obtain N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-(4-formylphenyl)-6-(isopropylamino)isonicotinamide (0.6 g, 85.7%).

Workup

  1. customreaction mass
  2. custompurged for 15 min with argon
  3. customargon was purged again for 10 min
  4. customReaction mass
  5. customOn completion, reaction mass
  6. filtrationfiltered through celite and celite bed
  7. washwashed with ethyl acetate
  8. dry with materialCombined filtrates were dried over Na2SO4 and solvent
  9. customremoved under reduced pressure
  10. customto afford crude material which
  11. customwas purified by column over silica gel

Sources & evidence

ORD record
ord-87ec377df63147c9969999c11bc48c70
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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