Piperazine → 3-[4-(4-Fluorophenyl)-6-piperazin-1-yl-2-(trifluoromethyl)pyrimidin-5-yl]benzenesulfonamide

HRID 251418Notes

Reaction equation

HRID 251418 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:9]=[C:10]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=2)=[C:6]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[N:5]=[C:4]([C:25]([F:28])([F:27])[F:26])[N:3]=1.[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C(#N)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:6]2[C:7]([C:8]3[CH:9]=[C:10]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=3)=[C:2]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[N:3]=[C:4]([C:25]([F:28])([F:27])[F:26])[N:5]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 58089378HCID 58089378, compound

Product 1

HCID 249590283-[4-(4-Fluorophenyl)-6-piperazin-1-yl-2-(trifluoromethyl)pyrimidin-5-yl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The solution of 3-[4-chloro-6-(4-fluorophenyl)-2-(trifluoromethyl)pyrimidin-5-yl]benzenesulfonamide (0.1 g, 0.24 mmol, prepared according to the procedure described above in preparation 4, Step 2a), in acetonitrile (2 ml) was treated with piperazine (0.104 g, 1.203 mmol) and the reaction mixture was stirred overnight at room temperature. Subsequently the reaction mixture was poured into ice-cold water and was extracted with ethylacetate (25 ml). The organic layer was washed with water, brine solution and then evaporated to obtain the title compound. 1H-NMR (DMSO-d6) δ: 2.58 (s, 4H), 3.19 (s, 4H), 7.03-7.14 (m, 4H), 7.32 (d, 1H), 7.41 (brs, D2O exchangeable, 2H), 7.46-7.50 (t, 1H), 7.72 (s, 1H), 7.73 (d, 1H). MS m/z: 482.1 (M++1).

Workup

  1. additionSubsequently the reaction mixture was poured into ice-cold water
  2. extractionwas extracted with ethylacetate (25 ml)
  3. washThe organic layer was washed with water, brine solution
  4. customevaporated

Sources & evidence

ORD record
ord-c80d026237f14a309a8c78301281efb6
Source dataset
uspto-grants-2011_01
Patent number
US07863446B2

Reaction notes

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