2-[4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]propanoic acid → 2-[4-chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]propan-1-one

HRID 710621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710621
[Cl:1][C:2]1[C:3]([C:13]([F:16])([F:15])[F:14])=[N:4][N:5]([CH:8]([CH3:12])[C:9]([OH:11])=O)[C:6]=1[CH3:7].[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[CH2:31][CH2:30][CH2:29][NH:28][C:27]=3[CH:26]=[N:25]2)=[CH:20][CH:19]=1>>[Cl:1][C:2]1[C:3]([C:13]([F:16])([F:15])[F:14])=[N:4][N:5]([CH:8]([CH3:12])[C:9]([N:28]2[CH2:29][CH2:30][CH2:31][C:32]3[N:24]([C:21]4[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=4)[N:25]=[CH:26][C:27]2=3)=[O:11])[C:6]=1[CH3:7]

Komponenten

3

Edukt 2

HCID 170245572-[4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]propanoic acidHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Produkt 1

HCID 733353332-[4-chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]propan-1-oneAusbeute 75 %

Versuchsvorschrift

The title compound was prepared from 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method B. The product mixture was washed with 2×1 M NaHSO4. The reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes) to provide 137 mg (75%) of the title compound as a white foam. 1H NMR (400 MHz, CDCl3) δ 8.41 (s, 1H), 7.43 (m, 2H), 7.15 (m, 2H), 5.52 (q, J=7.0 Hz, 1H), 3.75 (m, 1H), 3.41 (m, 1H), 2.81 (m, 2H), 2.28 (s, 3H), 1.85-1.99 (m, 2H), 1.81 (d, J=7 Hz, 1H); MS: (ES) m/z calculated for C20H19ClF4N5O [M+H]+ 456.1, found 456.1.

Aufarbeitung

  1. washThe product mixture was washed with 2×1 M NaHSO4
  2. customThe reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9ce3e73ff6d34ef7b1b148b67f37323e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181241B2

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