Ethyl Acetate → HCID 66990363, compound

HRID 454740Notes

Reaction equation

HRID 454740 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([C:13]2[CH:14]=[C:15]([C:19]([OH:21])=O)[CH:16]=[N:17][CH:18]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:22][C:23]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:40][CH3:41])[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26].C(OCC)(=O)C>O1CCCC1.CN(C)C=O.N1C=CC=CC=1.O>[C:45]([O:44][C:42]([N:39]([CH2:40][CH3:41])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[C:31]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([NH:22][C:19]([C:15]2[CH:16]=[N:17][CH:18]=[C:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:14]=2)=[O:21])[CH:32]=1)=[O:43])([CH3:48])([CH3:47])[CH3:46]

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 3461605-Phenylnicotinic AcidHCID 66990413HCID 66990413, compound

Product 1

HCID 66990363HCID 66990363, compoundYield 72.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under ice-cooling, oxalyl chloride (0.23 mL) was added to a solution mixture of 5-phenylpyridine-3-carboxylic acid (0.48 g) in tetrahydrofuran (4.8 mL) and N,N-dimethylformamide (0.010 mL), followed by stirring at room temperature for 40 minutes. The reaction mixture was added to a solution mixture of methyl 2-amino-4-(2-((tert-butoxycarbonyl)(ethyl)amino)phenyl)benzoate (0.80 g) in tetrahydrofuran (8.0 mL) and pyridine (0.44 mL) under ice-cooling, followed by stirring at room temperature for 1 hour and 10 minutes. Ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 85-70% hexane/ethyl acetate] to obtain 0.86 g of methyl 4-(2-((tert-butoxycarbonyl)(ethyl)amino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 1 hour and 10 minutes
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [eluent: 85-70% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-ccb9335cb56c4b2f9ed18822fae6a233
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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