Water → (2S)-2-Methyl-1-{[6-(methyloxy)-3-pyridinyl]carbonyl}-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 43400노트

반응식

HRID 43400 반응식
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3]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.[CH3:56][O:57][C:58]1[N:63]=[CH:62][C:61]([C:64](O)=[O:65])=[CH:60][CH:59]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][C@H:2]1[CH2:3][N:4]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)(=[O:9])=[O:10])[CH2:5][CH2:6][N:7]1[C:64]([C:61]1[CH:62]=[N:63][C:58]([O:57][CH3:56])=[CH:59][CH:60]=1)=[O:65]

참가 물질

8

반응물 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5924996-Methoxynicotinic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59152086(S)-3-Methyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperazine

생성물 1

HCID 59161354(2S)-2-Methyl-1-{[6-(methyloxy)-3-pyridinyl]carbonyl}-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine수율 59.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (3S)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 2) (100 mg, 0.324 mmol) in DMF (5 ml) was added HOBT.H2O (49.7 mg, 0.324 mmol), HBTU (123 mg, 0.324 mmol), 6-(methyloxy)-3-pyridinecarboxylic acid (49.7 mg, 0.324 mmol) and DIPEA (0.170 ml, 0.973 mmol) and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was evaporated in vacuo. The residue was dissolved in DCM (50 ml), transferred to a separating funnel and the solution was washed with NaHCO3 (5 ml), twice. The organic layer was dried with magnesium sulphate which was removed by filtration and the filtrate evaporated to dryness in vacuo. The residual oil was dissolved in 1:1 MeCN/DMSO (1.8 ml) and purified by MDAP in two batches. The fractions containing the desired product were combined and evaporated to dryness in vacuo to yield the title compound (85 mg).

후처리

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in DCM (50 ml)
  3. customtransferred to a separating funnel
  4. washthe solution was washed with NaHCO3 (5 ml)
  5. dry with materialThe organic layer was dried with magnesium sulphate which
  6. customwas removed by filtration
  7. customthe filtrate evaporated to dryness in vacuo
  8. dissolutionThe residual oil was dissolved in 1:1 MeCN/DMSO (1.8 ml)
  9. custompurified by MDAP in two batches
  10. additionThe fractions containing the desired product
  11. customevaporated to dryness in vacuo

출처 및 근거

ORD 기록
ord-84ee72a8c74b43759da346d0469f2b93
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536183B2

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