Hydrazine hydrate (1:1) → benzyl 6-isopropyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate

HRID 15757

Reaktionsgleichung

Reaktionsgleichung von HRID 15757
ClC1C=CC(S([N:11]2[CH:16]([C:17]3[CH:22]=CC(F)=C[CH:18]=3)[CH2:15][C:14]3[NH:24][N:25]=[CH:26][C:13]=3[CH2:12]2)(=O)=O)=CC=1.FC1C=CC(C2CC(=O)CCN2[C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])=CC=1.ClC1C=CC(C2CC(=O)CCN2C(OCC2C=CC=CC=2)=O)=CC=1.FC1C=CC([Mg]Br)=CC=1.O.NN.N1CCC(=O)CC1>>[CH:17]([CH:16]1[N:11]([C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])[CH2:12][C:13]2[CH:26]=[N:25][NH:24][C:14]=2[CH2:15]1)([CH3:18])[CH3:22]

Komponenten

7

Edukt 6

HCID 24654Hydrazine hydrate (1:1)HCID 337214-PiperidoneHCID 167304765-(4-Chlorophenylsulfonyl)-6-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridineHCID 21927691Benzyl 2-(4-fluorophenyl)-4-oxopiperidine-1-carboxylateHCID 59342393Benzyl 2-(4-chlorophenyl)-4-oxopiperidine-1-carboxylateHCID 178418676HCID 178418676, Verbindung

Produkt 1

HCID 68503449benzyl 6-isopropyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate

Versuchsvorschrift

5-(4-Chlorophenylsulfonyl)-6-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (Enantiomers A and B) Benzyl 2-(4-fluorophenyl)-4-oxopiperidine-1-carboxylate, prepared as described for compound 67 in Example using 4-fluorophenylmagnesium bromide, was formylated and treated with hydrazine hydrate as described for compound 50 in Example 1 to give benzyl 6-isopropyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate. This compound was then deprotected and treated with 4-chlorophenylsulfonyl chloride followed by NaOH as described for compound 52 in Example 1. The enantiomers were separated using HPLC Method [2].

Quellen und Nachweise

ORD-Eintrag
ord-4ede1439ca0e4b1785d47e42139e61a1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732609B2

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