Potassium Carbonate → 3-Formyl-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-benzoic acid methyl ester

HRID 583388Notes

Reaction equation

HRID 583388 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14].Cl.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]Cl)[CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]=1[N:12]([S:13]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)(=[O:14])=[O:15])[CH2:32][C:28]1[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 543619953-Formyl-2-(4-methoxy-benzenesulfonylamino)-benzoic acid methyl ester

Product 1

HCID 867543163-Formyl-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-benzoic acid methyl esterYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.20 g (0.573 mmol) of the product of Example 321 in 2.5 mL of DMF was added 0.099 g (0.602 mmol) of 3-picolyl chloride hydrochloride and 0.249 g (1.805 mmol) of potassium carbonate. The reaction was stined for 18 h at room temperature and then the reaction was then diluted with water and extracted with ether. The combined organics were washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with ether to give 0.158 g (63%) of the product as tan crystals. Electrospray Mass Spec: 440.9 (M+H)+.

Workup

  1. extractionextracted with ether
  2. washThe combined organics were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-795f9948a88c41d68bcff5a00100439b
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

Loading…