HCID 17973478, compound → N-(1,2,4-thiadiazol-5-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamide

HRID 1876680Notes

Reaction equation

HRID 1876680 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].Cl.[S:24]1[C:28]([NH2:29])=[N:27][CH:26]=[N:25]1>N1C=CC=CC=1>[S:24]1[C:28]([NH:29][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH:8]3[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C:2]([F:22])([F:21])[F:1])[CH2:6][CH2:7]3)=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[N:27][CH:26]=[N:25]1

Participants

4

Reactant 2

HCID 17973478HCID 17973478, compoundHCID 220145431,2,4-Thiadiazol-5-amine--hydrogen chloride (1/1)

Product 1

HCID 59465762N-(1,2,4-thiadiazol-5-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamideYield 13%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared using general procedure 15, method A. Under an N2 atmosphere, a mixture of 4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzene-1-sulfonyl chloride (13.0 g, 36.5 mmol), 1,2,4-thiadiazol-5-amine hydrochloride (5.0 g, 36.5 mmol), and pyridine (10 mL) was stirred at RT for 19 h. The crude product was purified via silica gel chromatography using 5% MeOH in CH2Cl2 giving N-(1,2,4-thiadiazol-5-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamide as a clear oil (2.0 g). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=421.1; tR=2.85 min.

Workup

  1. customPrepared
  2. customThe crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-5d1218d6d0ab428baf8d24f7f92af909
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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