Diisopropylethylamine → 4-[4-(4,5-Dihydro-1H-imidazol-2-yl)-piperazin-1-yl]-1-(phenylsulfonyl)-1H-indole

HRID 225426Notes

Reaction equation

HRID 225426 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I.CS[C:28]1[NH:29][CH2:30][CH2:31][N:32]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[NH:32]1[CH2:31][CH2:30][N:29]=[C:28]1[N:22]1[CH2:23][CH2:24][N:19]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[CH:12]=[CH:11][N:10]3[S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 101543921-(Phenylsulfonyl)-4-(1-piperazinyl)-1h-indoleHCID 122212281H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1)

Product 1

HCID 221748214-[4-(4,5-Dihydro-1H-imidazol-2-yl)-piperazin-1-yl]-1-(phenylsulfonyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-(phenylsulfonyl)-4-piperzin-1-yl-1H-indole (71 mg, 0.18 mmol) in dioxane is treated with 2-methylthio-2-imidazoline hydroiodide (52.7 mg, 0.22 mmol) and N,N-diisopropylethylamine (62 μl, 0.36 mmol), heated at 50° C. for 16 hr., cooled and concentrated in vacuo to give a residue. The residue is purified by HPLC to give the title product, 15 mg, identified by HPLC and mass spectral analyses (2.57 min; 410 M+H) using the LCMS conditions described in Table I.

Workup

  1. temperature, cooled
  2. concentrationconcentrated in vacuo
  3. customto give a residue
  4. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-34dc52177d7e4b9b837d853360c2c0c0
Source dataset
uspto-grants-2009_07
Patent number
US07557098B2

Reaction notes

Loading…