1-(6-Chloro-pyridine-3-sulfonyl)-4-methyl-piperazine → 3-{5-[(4-Methylpiperazin-1-yl)sulfonyl]pyridin-2-yl}-5-(2-methyl-1,3-thiazol-4-yl)-1H-indol-2-ol hydrochloride

HRID 748551

Reaction equation

HRID 748551 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:18][C:19]1[S:20][CH:21]=[C:22]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[NH:29][C:28](=[O:33])[CH2:27]3)[N:23]=1>>[ClH:1].[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([C:27]3[C:26]4[C:30](=[CH:31][CH:32]=[C:24]([C:22]5[N:23]=[C:19]([CH3:18])[S:20][CH:21]=5)[CH:25]=4)[NH:29][C:28]=3[OH:33])=[N:7][CH:6]=2)(=[O:10])=[O:9])[CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 8224571-(6-Chloro-pyridine-3-sulfonyl)-4-methyl-piperazineHCID 93430135-(2-Methyl-1,3-thiazol-4-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 1363421393-{5-[(4-Methylpiperazin-1-yl)sulfonyl]pyridin-2-yl}-5-(2-methyl-1,3-thiazol-4-yl)-1H-indol-2-ol hydrochlorideYield 35%

Procedure

The title compound was prepared as described for Example 101 using 1-[(6-chloropyridin-3-yl)sulfonyl]4-methylpiperazine (described in: Thunus L., Annales Pharmaceutiques Francaises 1977, 35, 197-203) and 5-(2-methyl-1,3-thiazol-4-yl)-1,3-dihydro-2H-indol-2-one. The crude product was purified on a silica gel column using chloroform/methanol/conc NH3(aq), (50:3:0.3), as the eluent. The base was dissolved in chloroform/methanol and converted to the hydrochloride salt using HCl in diethyl ether (1 M). Yield: 35% of the title compound: MS (ES) m/z 470 (M++1).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified on a silica gel column
  3. dissolutionThe base was dissolved in chloroform/methanol

Sources & evidence

ORD record
ord-0ee60742a056402c86d837fe02022e0f
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Linked notes

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