2-Chloro-4-hydrazinylpyridine → (2S,4R)-1-[2-(2-Chloro-pyridin-4-yl)-5-methyl-2H-pyrazol-3-yl]-4-cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697750Notes

Reaction equation

HRID 1697750 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1[C:17](=S)[CH2:18][C:19](=O)[CH3:20])=[O:4].[Cl:23][C:24]1[CH:29]=[C:28]([NH:30][NH2:31])[CH:27]=[CH:26][N:25]=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1[C:17]1[N:30]([C:28]2[CH:27]=[CH:26][N:25]=[C:24]([Cl:23])[CH:29]=2)[N:31]=[C:19]([CH3:20])[CH:18]=1)=[O:4]

Participants

3

Reactant 2

HCID 211064422-Chloro-4-hydrazinylpyridineHCID 86646864(2S,4R)-4-Cyclopropylmethanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 86646871(2S,4R)-1-[2-(2-Chloro-pyridin-4-yl)-5-methyl-2H-pyrazol-3-yl]-4-cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 192 h, (2S,4R)-4-cyclopropylmethanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic acid methyl ester (example 445c) was reacted with (2-chloro-pyridin-4-yl)-hydrazine (CAS Reg. No. 700811-29-6) to give the title compound as brown solid. MS (ESI): m/z=439.4 [M+H]+.

Sources & evidence

ORD record
ord-2ccae0aad82a44248b780e4de8eb10d4
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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