Triethylamine → 5-(3-((3-(3-Chloro-phenyl)-propyl)-(Pyridine-3-sulfonyl)-amino)-propyl)-thiophene-2-carboxylic acid methyl ester

HRID 2117469Notes

Reaction equation

HRID 2117469 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].C(N(CC)CC)C.Cl.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:33]=1>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:38]([C:34]2[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=2)(=[O:40])=[O:39])=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 539001205-(3-(3-(3-Chloro-phenyl)-propylamino)-propyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 536947585-(3-((3-(3-Chloro-phenyl)-propyl)-(Pyridine-3-sulfonyl)-amino)-propyl)-thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(3-(3-(3-chloro-phenyl)-propylamino)-propyl)-thiophene-2-carboxylic acid methyl ester (from Preparation 8, 0.0855 g, 0.243 mmol), triethylamine (0.0541 g 0.534 mmol), and pyridine-3-sulfonyl chloride hydrochloride (from Preparation 2, 0.0572 g, 0.267 mmol) in 10 mL CH2Cl2 combined at 0° C. was stirred at room temperature overnight. The organic solution was washed with water, saturated NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound of Step A as an oil. MS 494 (M+1).

Workup

  1. customcombined at 0° C.
  2. washThe organic solution was washed with water, saturated NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88d477a80bf24914b8a43e922e7d1e45
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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