Pyridine → HCID 9912486, compound

HRID 1418146Notes

Reaction equation

HRID 1418146 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH:17]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][C:19]([OH:21])=O.N1C=CC=CC=1.[C:34]([C:38]1[CH:44]=[CH:43][C:42]([C:45](=[O:47])[NH2:46])=[CH:41][C:39]=1[NH2:40])([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl.C(OCC)C.C(Cl)Cl.C(OCC)C.CO.CN(C)C=O>[C:34]([C:38]1[CH:44]=[CH:43][C:42]([C:45](=[O:47])[NH2:46])=[CH:41][C:39]=1[NH:40][C:19](=[O:21])[CH2:18][CH:17]([C:10]1[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:9]=1[O:8][CH3:7])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH3:37])([CH3:35])[CH3:36]

Participants

10

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 193486062-t-Butyl-5-carbamoylanilineHCID 19348738HCID 19348738, compound

Product 1

HCID 9912486HCID 9912486, compoundYield 86.4%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

0.31 ml (3.57 mmol) of oxalyl chloride and a catalyic amount of dimethyl-formamide were added, with ice-cooling, to a solution of 350 mg (1.19 mmol) of 3-(2,4-dimethoxyphenyl)nonanoic acid (prepared as described in Preparation 42B), in 7 ml of methylene chloride and the reaction temperature was raised to room temperature at once. The resulting mixture was then stirred for 50 minutes. The solvent and an excess of the reagent were removed by distillation under reduced pressure, and the resulting residue was dissolved in 7 ml of methylene chloride. 0.48 ml (5.95 mmol) of pyridine were added to the solution, followed by 206 mg (1.07 mmol) of 2-t-butyl-5-carbamoylaniline (prepared as described in Preparation 38), all with ice-cooling, and the resulting mixture was stirred at the same temperature for 30 minutes. At the end of this time, the reaction mixture was diluted with diethyl ether, and the diluted solution was washed with 1N aqueous hydrochloric acid, with a 0.5N aqueous solution of sodium hydroxide, with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 25 g of silica gel using a gradient elution method, with mixtures of methylene chloride and methanol ranging from 100:2 to 100:4 by volume as the eluent, to give 433 mg (yield 86%) of the title compound as crystals, melting at 152°-153° C. (from methylene chloride-diethyl ether).

Workup

  1. customThe solvent and an excess of the reagent were removed by distillation under reduced pressure
  2. dissolutionthe resulting residue was dissolved in 7 ml of methylene chloride
  3. temperatureall with ice-cooling
  4. stirringthe resulting mixture was stirred at the same temperature for 30 minutes
  5. washthe diluted solution was washed with 1N aqueous hydrochloric acid, with a 0.5N aqueous solution of sodium hydroxide, with water and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialafter which it was dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was purified by column chromatography through 25 g of silica gel using
  9. washa gradient elution method

Sources & evidence

ORD record
ord-f1f974ff71a44ec69e42cdacbb66a0fd
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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