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

HRID 369091Notes

Reaction equation

HRID 369091 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([C:9](=O)[CH2:10][C:11](=O)[CH:12]([F:14])[F:13])[S:8][C:4]=2[CH:3]=1.Cl.[S:20]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][NH2:31])=[CH:26][CH:25]=1)(=[O:23])(=[O:22])[NH2:21]>>[F:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([C:9]3[N:30]([C:27]4[CH:26]=[CH:25][C:24]([S:20]([NH2:21])(=[O:23])=[O:22])=[CH:29][CH:28]=4)[N:31]=[C:11]([CH:12]([F:14])[F:13])[CH:10]=3)[S:8][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 232853641-(6-Fluorobenzothiazol-2-yl)-4,4-difluorobutane-1,3-dione

Product 1

HCID 232853834-[5-(6-fluorobenzothiazol-2-yl)-3-difluoromethyl-1H-pyrazol-1-yl]benzenesulfonamideYield 57%

Procedure

The procedure of Example 9 was repeated using 1-(6-fluorobenzothiazol-2-yl)-4,4-difluorobutane-1,3-dione and 4-sulfamoylphenylhydrazine hydrochloride as the starting materials to obtain 4-[5-(6-fluorobenzothiazol-2-yl)-3-difluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide (yield, 57%). NMR(DMSO-d6) δ:7.22 (1H, t, J=54.1 Hz), 7.39-7.47 (1H, m), 7.53 (1H, s), 7.56 (2H, brs), 7.75-7.80 (2H, m), 7.93-8.00 (3H, m), 8.09-8.13 (1H, m); mp 255° C. (ethanol-water)

Sources & evidence

ORD record
ord-0b0ea7f3522243ce9d2c455434e75fc0
Source dataset
uspto-grants-2000_10
Patent number
US06136831

Reaction notes

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