Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate → Benzyl 2-[3-chloro-5-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate

HRID 567827Notes

Reaction equation

HRID 567827 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5](=[O:9])[N:4]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:3]=1[CH3:21].[CH2:22]([N:26]1[CH2:30][CH2:29][CH2:28][C@@H:27]1[CH2:31][NH2:32])[CH:23]([CH3:25])[CH3:24]>>[Cl:1][C:2]1[N:7]=[C:6]([NH:32][CH2:31][C@H:27]2[CH2:28][CH2:29][CH2:30][N:26]2[CH2:22][CH:23]([CH3:25])[CH3:24])[C:5](=[O:9])[N:4]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:3]=1[CH3:21]

Participants

3

Reactant 2

HCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 59900551[(2R)-1-(2-methylpropyl)pyrrolidin-2-yl]methanamine

Product 1

HCID 59900523Benzyl 2-[3-chloro-5-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate

Procedure

The title compound was prepared by a similar method to preparation 42 from benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preperation 170 and [(2R)-1-isobutylpyrrolidinyl]methanamine [see preparation 60]. The crude product was purified by column chromatography on silica gel using ethyl acetate as the eluant, to afford the product as a yellow oil, (94%).

Workup

  1. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8e8e1f0704ca4fe08e8cbbfbdabf7b5e
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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