1-(6-Chloro-pyridine-3-sulfonyl)-4-methyl-piperazine → Ammonia

HRID 748548Notes

Reaction equation

HRID 748548 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1)#[N:2].[Cl:13][C:14]1[N:19]=[CH:18][C:17]([S:20]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1>>[NH3:2].[ClH:13].[OH:12][C:8]1[NH:9][C:10]2[C:6]([C:7]=1[C:14]1[CH:15]=[CH:16][C:17]([S:20]([N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)(=[O:22])=[O:21])=[CH:18][N:19]=1)=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[CH:11]=2

Participants

4

Reactant 2

HCID 8224571-(6-Chloro-pyridine-3-sulfonyl)-4-methyl-piperazineHCID 27733482-Oxindole-6-carbonitrile

Product 2

HCID 222AmmoniaHCID 1363421352-Hydroxy-3-{5-[(4-methylpiperazin-1-yl)sulfonyl]pyridin-2-yl}-1H-indole-6-carbonitrile hydrochloride

Procedure

The title compound was prepared as described for Example 55 using 6-cyanooxindole (1.5 equ) and 1-(6-chloropyridine-3-sulfonyl)-4-methylpiperazine (1 equ; described in: Thunus L., Annales Pharmaceutiques Francaises 1977, 35, 197-203). Purification on a silica gel column using chloroform/methanol/conc. NH3(aq), (76:23: 1), as the eluent gave the title compound as the base. The base was dissolved in acetone/chloroform/methanol and treated with 5 M HCl in diethyl ether. The hydrochloride was dried to afford 24 mg (5.1% yield) of title compound: 1H NMR (DMSO-d6, 400 MHz) δ 14.87 (s, 1 H), 11.00 (s, 1 H), 10.21 (s, 1 H), 8.62 (s, 1 H), 7.83 (s, 2 H), 7.73 (d, J=8 Hz, 1 H), 7.38 (d, J=8 Hz, 1 H), 7.23 (s, 1 H), 3.81-3.67 (m, 2 H), 3.57-3.38 (m, 2 H), 3.22-3.05 (m, 2 H), 2.97-2.85 (m, 2 H), 2.77 (s, 3 H).

Workup

  1. customThe title compound was prepared
  2. customPurification on a silica gel column

Sources & evidence

ORD record
ord-1081cd3652114fbf8793dd72dd579243
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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