Ytterbium triflate → 2-(4-{3-[5-Acetyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-2-hydroxy-propyl}-piperazin-1-yl)-benzonitrile

HRID 33582

Reaktionsgleichung

Reaktionsgleichung von HRID 33582
[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]1[C:13]2[CH2:12][CH2:11][N:10]([C:14](=[O:16])[CH3:15])[CH2:9][C:8]=2[C:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)=[N:6]1.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[C:52]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=1[N:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1)#[N:53].CO.C(Cl)Cl>C(Cl)Cl.O>[C:14]([N:10]1[CH2:11][CH2:12][C:13]2[N:5]([CH2:4][CH:2]([OH:1])[CH2:3][N:63]3[CH2:62][CH2:61][N:60]([C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=4[C:52]#[N:53])[CH2:65][CH2:64]3)[N:6]=[C:7]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=3)[C:8]=2[CH2:9]1)(=[O:16])[CH3:15]

Komponenten

7

Edukt 4

HCID 2733225Ytterbium triflateHCID 2735875N-(2-Cyanophenyl)piperazineHCID 21226129Dichloromethane methanolHCID 222938171-[1-Oxiranylmethyl-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone

Produkt 1

HCID 103028372-(4-{3-[5-Acetyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-2-hydroxy-propyl}-piperazin-1-yl)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1-[1-oxiranylmethyl-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone (0.84 g, 2.30 mmol) in CH2Cl2 (10 mL) was treated with ytterbium(III) triflate (0.29 g, 0.46 mmol) and 1-(2-cyanophenyl)-piperazine (0.75 g, 3.5 mmol) at 25° C. and stirred for 48 h before it was diluted with CH2Cl2 (100 mL) and H2O (50 mL). The organic layer was separated, washed with H2O (2×50 mL), dried over Na2SO4, and concentrated. Column chromatography (silica, 5% MeOH/CH2Cl2) afforded 1.15 g (90%) of light yellow crystals. TLC (silica, 10% MeOH/CH2Cl2): Rf=0.30. MS (electrospray): m/z 553.3 ([M+H]+, C29H31F3N6O2 requires 552.3). 1H NMR (CDCl3, 400 MHz, a mixture of two rotamers): 7.82 and 7.68 (AB pattern, Jab=8.2 Hz, 2H), 7.76 and 7.72 (AB pattern, Jab=8.4 Hz, 2H), 7.60-7.48 (m, 2H), 7.05-7.00 (m, 2H), 4.90 and 4.78 (AB pattern, Jab=16 Hz, 1H), 4.69 (s, 1H), 4.30-3.71 (m, 6H), 3.25 (m, 4H), 3.02-2.75 (m, 4H), 2.70-2.65 (m, 2H), 2.60-2.53 (m, 2H), 2.23 (s, 1.5H), 2.18 (s, 1.5H).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with H2O (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customColumn chromatography (silica, 5% MeOH/CH2Cl2) afforded 1.15 g (90%) of light yellow crystals

Quellen und Nachweise

ORD-Eintrag
ord-3107526c05cc47029b0d0c41b1554a0d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429591B2

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