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

HRID 748552Notes

Reaction equation

HRID 748552 reaction equation
Cl[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.[O:18]1[C:22]([C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][C:27](=[O:32])[CH2:26]3)=[CH:21][N:20]=[CH:19]1>>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([C:26]3[C:25]4[C:29](=[CH:30][CH:31]=[C:23]([C:22]5[O:18][CH:19]=[N:20][CH:21]=5)[CH:24]=4)[NH:28][C:27]=3[OH:32])=[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 11008941HCID 11008941, compound

Product 1

HCID 1363421413-{5-[(4-Methylpiperazin-1-yl)sulfonyl]pyridin-2-yl}-5-(1,3-oxazol-5-yl)-1H-indol-2-olYield 1%

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-(1,3-oxazol-5-yl)-1,3-dihydro-2H-indol-2-one. The crude product was purified on a silica gel column using chloroform/methanol/conc NH3(aq), (100:10:1), as the eluent followed by trituration in ethyl acetate. Yield: 1% of the title compound: MS (ES) m/z 441 (M++1).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-c793575710764953919a22c768d23887
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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