Triethylamine → HCID 67819598, compound

HRID 925292Notes

Reaction equation

HRID 925292 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[C:5]([O:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:4]=1.[CH2:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH3:24].[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[S:35](Cl)(=[O:37])=[O:36]>ClCCl>[CH2:19]([N:18]([CH2:21][CH3:22])[CH2:17][CH2:16][O:15][C:5]1[CH:4]=[C:3]([CH2:2][NH:1][S:35]([C:31]2[S:30][CH:34]=[CH:33][CH:32]=2)(=[O:37])=[O:36])[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=1)[CH3:20].[CH2:19]([N:18]([CH2:21][CH3:22])[CH2:17][CH2:16][O:15][C:5]1[CH:4]=[C:3]([CH2:2][N:1]([CH2:2][C:3]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[CH:6]=[C:5]([O:15][CH2:24][CH2:23][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH:4]=2)[S:35]([C:31]2[S:30][CH:34]=[CH:33][CH:32]=2)(=[O:37])=[O:36])[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=1)[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 67609537HCID 67609537, compound

Product 2

HCID 67609077HCID 67609077, compoundYield 22%HCID 67819598HCID 67819598, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of [2-(6-Aminomethyl-[2,2′]bipyridinyl-4-yloxy)-ethyl]-diethylamine (107 mg, 0.357 mmol), triethylamine (136.5 μL, 1.07 mmol), Thiophene-2-sulfonyl chloride (195.4 mg, 1.07 mmol) and dichloromethane (5 mL) was stirred at 25° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and the crude purified by column chromatography on silica gel (0-10% methanol in dichloromethane) to afford thiophene-2-sulfonic acid [4-(2-diethylamino-ethoxy)-[2,2′]bipyridinyl-6-ylmethyl]-amide as a yellow oil (85.0 mg, 53%) and thiophene-2-sulfonic acid bis-[4-(2-diethylamino-ethoxy)-[2,2′]bipyridinyl-6-ylmethyl]-amide as a brown oil (58.7 mg, 22%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude purified by column chromatography on silica gel (0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-bfd1ede909c941a3b2b6922d75e0e092
Source dataset
uspto-grants-2016_03
Patent number
US09284296B2

Reaction notes

Loading…