1-(5-Nitropyridin-2-yl)piperazine → HCID 25004371, compound

HRID 72678Notes

Reaction equation

HRID 72678 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.[N+:28]([C:31]1[CH:32]=[CH:33][C:34]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[N:35][CH:36]=1)([O-:30])=[O:29]>N1C=CC=CC=1>[N+:28]([C:31]1[CH:32]=[CH:33][C:34]([N:37]2[CH2:38][CH2:39][N:40]([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)[CH2:41][CH2:42]2)=[N:35][CH:36]=1)([O-:30])=[O:29]

Participants

4

Reactant 2

HCID 29287991-(5-Nitropyridin-2-yl)piperazineHCID 866136213-[6-Chloro-5-phenyl-2-(trifluoromethyl)pyrimidin-4-yl]benzenesulfonamide

Product 1

HCID 25004371HCID 25004371, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 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-nitropyridin-2-yl)piperazine (0.075 g, 0.363 mmol) and stirred for 11 hours. Subsequently the reaction mixture was poured onto ice-cold water and extracted with ethyl acetate (25 ml). The organic layer was washed with brine and evaporated to give the crude material. Purification by column chromatography (elution with 70% ethyl acetate in hexane) yielded the title compound. 1H-NMR (CDCl3) δ: 3.45-3.46 (m, 4H), 3.72 (m, 4H), 6.52-6.54 (d, 1H), 7.08-7.11 (d, 2H), 7.21-7.26 (m, 2H), 7.32-7.34 (d, 1H), 7.40-7.42 (d, 1H), 7.50 (m, 1H), 7.68 (s, 1H), 7.84-7.89 (m, 1H), 8.21-8.23 (d, 1H), 8.99 (s, 1H); MS m/z: 585.8 (M+).

Workup

  1. additionSubsequently the reaction mixture was poured onto ice-cold water
  2. extractionextracted with ethyl acetate (25 ml)
  3. washThe organic layer was washed with brine
  4. customevaporated
  5. customto give the crude material
  6. customPurification
  7. washby column chromatography (elution with 70% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c71cebf072604b6681de1c00a59ebdd7
Source dataset
uspto-grants-2014_09
Patent number
US08828999B2

Reaction notes

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