Pyridine → HCID 12052636, compound

HRID 1264071Notes

Reaction equation

HRID 1264071 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[NH2:24][C:25]1[CH:30]=[C:29]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH:28]=[CH:27][C:26]=1[NH:39][CH2:40][C:41]1[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[C:43]([O:51][CH3:52])[CH:42]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C>[Si:32]([O:31][C:29]1[CH:28]=[CH:27][C:26]([NH:39][CH2:40][C:41]2[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[C:43]([O:51][CH3:52])[CH:42]=2)=[C:25]([NH:24][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:17][CH:16]=2)[CH:30]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 65042284-(2-Pyrrolidin-1-yl-ethoxy)-benzoic acidHCID 12052621HCID 12052621, compound

Product 1

HCID 12052636HCID 12052636, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To 4-[2-(1-pyrrolidinyl)ethoxy]benzoic acid (350 mg, 1.29 mmol) in CH2Cl2 (2 ml) was added oxalyl chloride (327 mg, 2.58 mmol) and a catalytic amount of DMF. The mixture was stirred at room temperature for 1 h and then concentrated under reduced pressure. The acid chloride was dried, under vacuum, overnight. To the aniline (Example 1, Part D; 0.49 g, 1.17 mmol), in pyridine (0.158 g, 2.34 mmol) and CH2Cl2 (3 mL) at 0° C. and under N2, was added the previously formed acid chloride (see Example 5, Part D) in 4 mL CH2Cl2 dropwise. Upon completion of addition, the mixture was stirred for 15 minutes at room temperature and then the reaction quenched by the addition saturated NaHCO3. Product was extracted with EtOAc, the organics washed with H2O, and concentrated under reduced pressure; yielding 583 mg of desired product after flash chromatography (SiO2, 10% MeOH in CHCl3).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dry with materialThe acid chloride was dried, under vacuum, overnight
  3. additionUpon completion of addition
  4. stirringthe mixture was stirred for 15 minutes at room temperature
  5. customthe reaction quenched by the addition saturated NaHCO3
  6. extractionProduct was extracted with EtOAc
  7. washthe organics washed with H2O
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6144360360444370b0be26e942779052
Source dataset
uspto-grants-2003_04
Patent number
US06541499B1

Reaction notes

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