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

HRID 15756

Reaktionsgleichung

Reaktionsgleichung von HRID 15756
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH:12]1[C:18]1[CH:23]=CC=C(F)[CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC(S(N2C(C3C=CC=C(F)C=3)C[C:38]3[NH:48][N:49]=CC=3C2)(=O)=O)=CC=1.ClC1C=CC(C2CC(=O)CCN2C(OCC2C=CC=CC=2)=O)=CC=1.FC1C=C([Mg]Br)C=CC=1.O.NN.N1CCC(=O)CC1>>[CH:18]([CH:12]1[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:16][C:15]2[CH:38]=[N:48][NH:49][C:14]=2[CH2:13]1)([CH3:19])[CH3:23]

Komponenten

6

Edukt 5

HCID 24654Hydrazine hydrate (1:1)HCID 337214-PiperidoneHCID 59342393Benzyl 2-(4-chlorophenyl)-4-oxopiperidine-1-carboxylateHCID 685013455-(4-Chlorophenylsulfonyl)-6-(3-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine Benzyl 2-(3-fluorophenyl)-4-oxopiperidine-1-carboxylateHCID 178505773HCID 178505773, Verbindung

Produkt 1

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

Versuchsvorschrift

5-(4-Chlorophenylsulfonyl)-6-(3-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine Benzyl 2-(3-fluorophenyl)-4-oxopiperidine-1-carboxylate, prepared as described for compound 67 in Example 3 using (3-fluorophenyl)magnesium 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.

Quellen und Nachweise

ORD-Eintrag
ord-a83659f4c2464fc4998c42480e6ec250
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732609B2

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