Pyridine → HCID 54008307, compound

HRID 480303Notes

Reaction equation

HRID 480303 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8](=[O:19])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][NH2:18])=[CH:11][CH:10]=1.N1C=CC=CC=1.CCOC(C)=O>C(Cl)Cl>[CH3:6][O:7][C:8](=[O:19])[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][NH:18][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 14097616Methyl 4-(2-aminoethoxy)benzoate

Product 1

HCID 54008307HCID 54008307, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (144 mg, 1.27 mmol) was added to a solution of 4-(2-amino-ethoxy)-benzoic acid methyl ester (266 mg, 1.15 mmol) and pyridine (255 mg, 2.52 mmol) in CH2Cl2 (10 mL) at 0° C. The solution was warmed to room temperature and was stirred for 24 h. EtOAc was added and the organic solution was washed with HCl (1N, 2×) followed by brine. The organic solution was dried (Na2SO4), filtered, and concentrated to yield the title compound as a white solid (240 mg). 1H NMR (400 MHz, CDCl3) δ 7.99 (dd, 2H), 6.90 (dd, 2H), 4.77 (m, 1H), 4.15 (t, 2H), 3.88 (s, 3H), 3.58 (m, 2H), 3.02 (s, 3H); MS 274 (M+1).

Workup

  1. washthe organic solution was washed with HCl (1N, 2×)
  2. dry with materialThe organic solution was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d05e9e44dd7481280b94e77b52aa0b5
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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