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

HRID 72674
Notes
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Reaction equation

HRID 72674 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 1049
Pyridine
Solvent

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-a240d3e678cf43de9dd5c77babba9180
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08828999B2

Reaction notes

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