Water → 1-[(2-Methyl-4-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 41313

반응식

HRID 41313 반응식
[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.[CH3:55][C:56]1[CH:61]=[C:60]([C:62](O)=[O:63])[CH:59]=[CH:58][N:57]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[CH3:55][C:56]1[CH:61]=[C:60]([C:62]([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:63])[CH:59]=[CH:58][N:57]=1

참가 물질

9

반응물 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 25545781-[4-(Trifluoromethyl)benzenesulfonyl]piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27628212-Methylpyridine-4-carboxylic acid

생성물 1

HCID 446120801-[(2-Methyl-4-pyridinyl)carbonyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine수율 57.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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), 2-methyl-4-pyridinecarboxylic acid (46.6 mg, 0.340 mmol) and DIPEA (0.178 ml, 1.02 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 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 (81 mg).

후처리

  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 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

출처 및 근거

ORD 기록
ord-8dc7e5fd601245d8a35ff0dac3ebe8f0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530478B2

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