Pyridine → HCID 86696298, compound

HRID 882353Notes

Reaction equation

HRID 882353 reaction equation
[C:1](Cl)(=[O:6])[O:2][CH:3]([Cl:5])[CH3:4].[CH3:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.N1C=CC=CC=1>C(Cl)Cl>[ClH:5].[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([C:1]([O:2][CH:3]([Cl:5])[CH3:4])=[O:6])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 531671-MethylpiperazineHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 86696298HCID 86696298, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in Example 3, 1-chloroethyl carbonochloridate was reacted with 1-methylpiperazine and pyridine in methylene chloride at −78° C. for 3 h to give 1-chloroethyl 4-methylpiperazine-1-carboxylate hydrochloride salt which was reacted with chiral 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoic acid in the presence of cesium carbonate in dimethylformamide overnight to give, after flash chromatography purification (hexane/ethyl acetate, 80/20 to 20/80), 4-methyl-piperazine-1-carboxylic acid 1-(4-{[(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-3-methoxy-benzoyloxy)-ethyl ester as a white solid. LCMS (ES+) m/z calcd. for C39H44Cl2F2N5O6 [(M+H)+]: 786, found: 786.

Sources & evidence

ORD record
ord-ea86c529342b498e819ae02784a91c47
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

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