4-Hydrazinylbenzenesulfonamide hydrochloride → 4-[5-(6-methoxybenzothiazol-2-yl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide

HRID 369081

Reaction equation

HRID 369081 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3](=O)[CH2:4][C:5]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)=O.Cl.[S:22]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][NH2:33])=[CH:28][CH:27]=1)(=[O:25])(=[O:24])[NH2:23]>>[CH3:17][O:16][C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([C:5]3[N:32]([C:29]4[CH:28]=[CH:27][C:26]([S:22]([NH2:23])(=[O:25])=[O:24])=[CH:31][CH:30]=4)[N:33]=[C:3]([C:2]([F:20])([F:19])[F:1])[CH:4]=3)[S:8][C:9]=2[CH:15]=1

Participants

3

Reactant 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 154910984,4,4-Trifluoro-1-(6-methoxybenzothiazol-2-yl)butane-1,3-dione

Product 1

HCID 154910994-[5-(6-methoxybenzothiazol-2-yl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide

Procedure

The procedure of Example 9 was repeated using 4,4,4-trifluoro-1-(6-methoxybenzothiazol-2-yl)butane-1,3-dione and 4-sulfamoylphenylhydrazine hydrochloride as the starting materials to obtain 4-[5-(6-methoxybenzothiazol-2-yl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide. NMR(CDCl3) δ: 3.88 (3H, s), 5.03 (2H, bs), 7.11 (1H, dd, J=2.3 Hz, 8.9 Hz), 7.20 (1H, s), 7.31 (2H, d, J=2.3 Hz), 7.68 (2H, d, J=8.6 Hz), 7.83 (1H, d, J=8.9 Hz), 8.01 (2H, d, J=8.6 Hz); mp 236-237° C. (ethyl acetate-isooctane)

Sources & evidence

ORD record
ord-ecbce7ed4cf544fd8510da76b509525e
Source dataset
uspto-grants-2000_10
Patent number
US06136831

Linked notes

Loading…