Hydrazine → 4-({4-[2-(1-Piperidinyl)ethoxy]-1H-indazol-1-yl}sulfonyl)aniline

HRID 896296Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:21]3[C:16](=[C:17]([O:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[CH:18]=[CH:19][CH:20]=3)[CH:15]=[N:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.NN>CO.[Ni]>[N:25]1([CH2:24][CH2:23][O:22][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:16]=2[CH:15]=[N:14][N:13]3[S:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)(=[O:11])=[O:12])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of 1-[(4-nitrophenyl)sulfonyl]-4-[2-(1-piperidinyl)ethoxy]1H-indazole (0.39 g, 0.91 mol) in methanol is treated with Raney Nickel followed by hydrazine (0.2 ml, 6.3 mmol), stirred at 0° C. for 2 hr and decanted. The catalyst is washed with a methanol: methylene chloride 3:7 mixture. The washes and supernatant are combined and concentrated in vacuo. The resultant residue is purified by flash chromatography (silicagel, EtOAc/2M NH3 in methanol 8:2) to give the title product as a white solid, 0.15 g, mp 149-150° C. (dec), identified by NMR and mass spectral analyses.

Workup

customdecanted
washThe catalyst is washed with a methanol: methylene chloride 3:7 mixture
concentrationconcentrated in vacuo
customThe resultant residue is purified by flash chromatography (silicagel, EtOAc/2M NH3 in methanol 8:2)

Sources & evidence

ORD record: ord-5c124ee5056e429abe4936b63c2f0e2e
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919354B2

Reaction notes

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