Hydrochloric Acid → 3-[6-{4-[5-(Trifluoromethyl)pyridin-2-yl]piperazin-1-yl}-5-phenyl-2-(trifluoromethyl)pyrimidin-4-yl]benzenesulfonamide

HRID 1966341Notes

Reaction equation

HRID 1966341 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:13]=[C:14]([S:18]([NH2:21])(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=2)[C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[F:28][C:29]([F:43])([F:42])[C:30]1[CH:31]=[CH:32][C:33]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[N:34][CH:35]=1.Cl>N1C=CC=CC=1>[F:43][C:29]([F:28])([F:42])[C:30]1[CH:31]=[CH:32][C:33]([N:36]2[CH2:37][CH2:38][N:39]([C:2]3[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]4[CH:13]=[C:14]([S:18]([NH2:21])(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=4)[C:3]=3[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:40][CH2:41]2)=[N:34][CH:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6676181-(5-Trifluoromethyl-pyridin-2-yl)-piperazineHCID 866136213-[6-Chloro-5-phenyl-2-(trifluoromethyl)pyrimidin-4-yl]benzenesulfonamide

Product 1

HCID 250043693-[6-{4-[5-(Trifluoromethyl)pyridin-2-yl]piperazin-1-yl}-5-phenyl-2-(trifluoromethyl)pyrimidin-4-yl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-[6-chloro-5-phenyl-2-(trifluoromethyl)pyrimidin-4-yl]benzenesulfonamide (0.1 g, 0.242 mmol) in pyridine (2 ml) was treated with 1-[5-(trifluoromethyl)pyridin-2-yl]piperazine (0.3 g, 0.68 mmol) and the reaction mixture was stirred for 1 hour at room temperature. Subsequently the reaction mixture was poured onto crushed ice containing two drops of concentrated hydrochloric acid, extracted with ethyl acetate (25 ml) and the organic layer was washed with brine and evaporated. The title compound was obtained by column chromatographic purification of the crude material with 30% ethyl acetate in hexane. 1H-NMR (DMSO-d6) δ: 3.33-3.37 (m, 4H), 3.56 (m, 4H), 6.86-6.88 (d, 1H), 7.10-7.12 (d, 2H), 7.22-7.29 (m, 3H), 7.35-7.37 (m, 1H), 7.44-7.48 (m, 1H), 7.74-7.79 (m, 3H), 8.38 (s, 1H); MS m/z: 608.8 (M+).

Workup

  1. additionSubsequently the reaction mixture was poured
  2. extractionextracted with ethyl acetate (25 ml)
  3. washthe organic layer was washed with brine
  4. customevaporated

Sources & evidence

ORD record
ord-8b03bb53b33141619a375584ec464c45
Source dataset
uspto-grants-2013_04
Patent number
US08420653B2

Reaction notes

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