4-Chlorobenzenesulfonyl chloride → 5-(4-Chlorophenylsulfonyl)-6-isopropyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

HRID 15750Notes

Reaction equation

HRID 15750 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].C(OC([N:21]1[CH:26]([C:27]2[CH:32]=CC=C[CH:28]=2)[CH2:25][C:24]2[NH:33][N:34]=[CH:35][C:23]=2[CH2:22]1)=O)(C)(C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:21]2[CH:26]([CH:27]([CH3:32])[CH3:28])[CH2:25][C:24]3[NH:33][N:34]=[CH:35][C:23]=3[CH2:22]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 593424006-Phenyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 167304755-(4-Chlorophenylsulfonyl)-6-isopropyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

Procedure

Benzyl 2-isopropyl-4-oxopiperidine-1-carboxylate, prepared as described for compound 67 in Example 3 using isopropylmagnesium chloride, 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.

Sources & evidence

ORD record
ord-45c63dd009ce4538878d4f0f39363b01
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Reaction notes

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