Triethylamine → N-2-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]ethyl-4-phenoxybenzenesulfonamide

HRID 724695Notes

Reaction equation

HRID 724695 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:21](=[O:23])(=[O:22])[N:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:19](=[O:28])[CH:18]=2)=[CH:13][CH:12]=1.C(N(CC)CC)C.[O:36]([C:43]1[CH:48]=[CH:47][C:46]([S:49](Cl)(=[O:51])=[O:50])=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C)C=O>[C:24]([N:20]1[C:19](=[O:28])[CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][NH:8][S:49]([C:46]3[CH:45]=[CH:44][C:43]([O:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:48][CH:47]=3)(=[O:51])=[O:50])=[CH:12][CH:13]=2)[S:21]1(=[O:23])=[O:22])([CH3:25])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27947564-Phenoxybenzene-1-sulfonyl chlorideHCID 218793835-[4-(2-aminoethyl)phenyl]-2-tert-butylisothiazol-3(2H)-one 1,1-dioxide Trifluoroacetate

Product 1

HCID 21878718N-2-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]ethyl-4-phenoxybenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[4-(2-Aminoethyl)phenyl]-2-tert-butylisothiazol-3(2H)-one 1,1-dioxide trifluoroacetate (36.7 mg, 0.0869 mmol) and triethylamine (36.3 μL, 0.260 mmol) were dissolved in N,N-dimethylformamide (0.15 mL). 4-Phenoxybenzenesulfonyl chloride (29.2 mg, 0.109 mmol) was added and the reaction was allowed to stir at room temperature for 30 minutes. The reaction was chromatographed on a 21.2 mm Luna C18 column using a 10–90% acetonitrile in water gradient with 0.05% trifluoroacetic acid at 12.5 mL per minute over a 15 minute period. The major fraction was evaporated to a clear glass (18 mg, 38%). 1H NMR (500 MHz, CDCl3): δ 7.75 (d, J=8.8 Hz, 2H), 7.69 (d, J=8.3 Hz, 2H), 7.41 (t, J=8.1 Hz, 2H), 7.27 (d, J=7.8 Hz, 3H), 7.23 (t, J=7.6 Hz, 1H), 7.07 (d, J=7.8 Hz, 2H), 7.02 (d, J=8.8 Hz, 2H), 3.25 (t, J=6.8 Hz, 2H), 2.87 (t, J=7.1 Hz, 2H), 1.73 (s, 9H); LCMS found for C27H32N3O6S2 (M+NH4)+: m/z 558.2.

Workup

  1. customThe reaction was chromatographed on a 21.2 mm Luna C18 column
  2. customover a 15 minute
  3. customThe major fraction was evaporated to a clear glass (18 mg, 38%)

Sources & evidence

ORD record
ord-83e17194ce944fc58a8207bce85a3458
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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