Sodium Carbonate → HCID 70872754, compound

HRID 1959301Notes

Reaction equation

HRID 1959301 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:22]([CH2:29][CH2:30][O:31][CH3:32])[CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]([CH3:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])=[O:8].[O:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=2)[CH2:35][CH2:34]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[CH3:17][C:16]1[CH:15]=[C:14]([CH3:18])[NH:13][C:12](=[O:19])[C:11]=1[CH2:10][NH:9][C:7]([C:6]1[CH:20]=[C:2]([C:43]2[CH:42]=[CH:41][C:40]([CH2:39][N:36]3[CH2:37][CH2:38][O:33][CH2:34][CH2:35]3)=[CH:45][CH:44]=2)[CH:3]=[C:4]([N:22]([CH2:29][CH2:30][O:31][CH3:32])[CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]=1[CH3:21])=[O:8]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10998582{4-[(Morpholin-4-yl)methyl]phenyl}boronic acidHCID 70872486HCID 70872486, compound

Product 1

HCID 70872754HCID 70872754, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-((2-methoxyethyl)(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzamide (110 mg, 0.21 mmol), (4-(morpholinomethyl)phenyl)boronic acid (99 mg, 0.33 mmol), sodium carbonate (83 mg, 0.78 mmol) in 4 ml of dioxane was degassed with argon for 20 min, Pd(PPh3) (25 mg, 0.02 mmol) was added to the mixture and heated to 100° C. for overnight. The reaction was cooled to room temperature and diluted with water, compound was extracted in 10% MeOH in DCM, dried over Na2SO4, concentrated and crude product purified by silica gel (100-200) chromatography to obtain the title compound (50 mg 38%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionwas extracted in 10% MeOH in DCM
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customcrude product purified by silica gel (100-200) chromatography

Sources & evidence

ORD record
ord-d47f7049013d4d1ab3063be51a4f87c8
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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