Triethylamine → HCID 53870459, compound

HRID 2300445Notes

Reaction equation

HRID 2300445 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[CH:8][CH:9]=1)=[O:4].[CH:24]1([S:27](Cl)(=[O:29])=[O:28])[CH2:26][CH2:25]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[S:27]([CH:24]2[CH2:26][CH2:25]2)(=[O:29])=[O:28])=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 2760919Cyclopropanesulfonyl chloride2×HCID 539001205-(3-(3-(3-Chloro-phenyl)-propylamino)-propyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 53870459HCID 53870459, compoundYield 117.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-{3-[3-(3-chloro-phenyl)-propylamino]-propyl}-thiophene-2-carboxylic acid methyl ester (51.5 mg, 0.1463 mmol), of Preparation 8, in CH2Cl2 (10 mL) at 0° C. was added cyclopropanesulfonyl chloride (22.6 mg, 0.161 mmol) and triethylamine (0.45 mL, 0.32 mmol). The reaction was warmed to room temperature and was stirred for 48 h. The reaction was heated at reflux for 48 h and additional triethylamine (0.45 mL) and cyclopropanesulfonyl chloride (22.6 mg) were added. The reaction was heated at reflux for 7.5 h, was cooled to room temperature and was stirred for 72 h. The reaction was heated at reflux for 24 h. The organic solution was washed sequentially with 5.5% aqueous HCl, water, saturated sodium bicarbonate solution, and brine. The organic solution was dried (MgSO4), filtered, and concentrated to provide the title compound of Step A (78.1 mg). MS 456 (M+).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 48 h
  3. temperatureThe reaction was heated
  4. temperatureat reflux for 7.5 h
  5. temperaturewas cooled to room temperature
  6. stirringwas stirred for 72 h
  7. temperatureThe reaction was heated
  8. temperatureat reflux for 24 h
  9. washThe organic solution was washed sequentially with 5.5% aqueous HCl, water, saturated sodium bicarbonate solution, and brine
  10. dry with materialThe organic solution was dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-f269b12ebd0e44ee9b7ef756dc192032
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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