Nicotinic Acid → 1-(3-Pyridinylcarbonyl)-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 43389

反応式

HRID 43389 の反応式
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:55]1[CH:60]=[CH:59][CH:58]=[C:57]([C:61](O)=[O:62])[CH:56]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[N:55]1[CH:60]=[CH:59][CH:58]=[C:57]([C:61]([N:15]2[CH2:16][CH2:17][N:12]([S:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:18])[F:19])=[CH:8][CH:7]=3)(=[O:10])=[O:11])[CH2:13][CH2:14]2)=[O:62])[CH:56]=1

参加物

9

反応物 6

HCID 938Nicotinic AcidHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 25545781-[4-(Trifluoromethyl)benzenesulfonyl]piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 93012951-(3-Pyridinylcarbonyl)-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine収率 46.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 1) (100 mg, 0.340 mmol) in DMF (5 ml) was added HOBT.H2O (52.0 mg, 0.340 mmol), HBTU (129 mg, 0.340 mmol), 3-pyridinecarboxylic acid (41.8 mg, 0.340 mmol) and DIPEA (0.178 ml, 1.019 mmol). The reaction mixture was stirred for 2 hours at room temperature. Reaction mixture was transferred to a 100 ml round bottom flask and was reduced to dryness in vacuo. The residue was dissolved in DCM (50 ml) and was transferred to a separating funnel then washed with saturated NaHCO3 solution (5 ml), twice. The organic layer was collected and dried with dried magnesium sulphate. The solid was removed by filtration and the filtrate collected in a 250 ml round bottom flask and reduced to dryness in vacuo. The residue was then dissolved in 1.8 ml 1:1 MeCN/DMSO and purified by MDAP in 2 batches. The fractions containing desired product were combined in a 250 ml round bottom flask and reduced in vacuo to yield the title compound (63 mg).

後処理

  1. customReaction mixture
  2. customwas transferred to a 100 ml round bottom flask
  3. customwas transferred to a separating funnel
  4. washthen washed with saturated NaHCO3 solution (5 ml)
  5. customThe organic layer was collected
  6. dry with materialdried with dried magnesium sulphate
  7. customThe solid was removed by filtration
  8. customthe filtrate collected in a 250 ml round bottom flask
  9. dissolutionThe residue was then dissolved in 1.8 ml 1:1 MeCN/DMSO
  10. custompurified by MDAP in 2 batches
  11. additionThe fractions containing desired product
  12. customwere combined in a 250 ml round bottom flask

出典と根拠

ORDレコード
ord-6aeb1a5456d549e0a4caad263df3e483
出典データセット
uspto-grants-2013_09
特許番号
US08536183B2

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