Sodium Carbonate → 6-[4-Methoxybenzyl-(6-morpholinopyridin-3-yl)amino]-4-[(trifluoroacetyl)amino]pyridine-3-carboxylic acid ethyl ester

HRID 2035546Notes

Reaction equation

HRID 2035546 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9](Cl)=[CH:10][C:11]=1[NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[O:5])[CH3:2].[CH3:20][O:21][C:22]1[CH:41]=[CH:40][C:25]([CH2:26][NH:27][C:28]2[CH:29]=[N:30][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:32][CH:33]=2)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]([N:27]([CH2:26][C:25]2[CH:40]=[CH:41][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[C:28]2[CH:29]=[N:30][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:32][CH:33]=2)=[CH:10][C:11]=1[NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 634876Binap, (A+-)-HCID 674131333-(4-Methoxybenzyl)amino-6-morpholinopyridineHCID 866579426-Chloro-4-(trifluoroacetyl)aminopyridine-3-carboxylic acid ethyl ester

Product 1

HCID 866579436-[4-Methoxybenzyl-(6-morpholinopyridin-3-yl)amino]-4-[(trifluoroacetyl)amino]pyridine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

21.8 mg of 6-chloro-4-(trifluoroacetyl)aminopyridine-3-carboxylic acid ethyl ester and 22 mg of 3-(4-methoxybenzyl)amino-6-morpholinopyridine were dissolved in 1 mL of toluene, to which 1.7 mg of palladium (II) acetate, 9.2 mg of 2,2′-bis (diphenylphosphino)-1,1′-binaphthyl and 202 mg of sodium carbonate were added, and stirred overnight at 100° C. After cooling, water was added to the reaction mixture, extracted with chloroform, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (hexane:ethyl acetate=1:1) to obtain 5.7 mg (ylod 14%) of the title compound as a light yellow solid.

Workup

  1. additionwere added
  2. temperatureAfter cooling
  3. extractionextracted with chloroform
  4. washthe extract was washed with saturated saline
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel thin layer chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-451822e827f04f6d9cb107ac04030ad2
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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