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

HRID 567828Notes

Reaction equation

HRID 567828 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH2:15][CH:16]([CH3:18])[CH3:17])[C:5](=[O:19])[N:4]([CH2:20][C:21]([O:23]CC2C=CC=CC=2)=[O:22])[C:3]=1[CH3:31]>[OH-].[Pd+2].[OH-]>[ClH:1].[CH2:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@@H:10]1[CH2:9][NH:8][C:6]1[C:5](=[O:19])[N:4]([CH2:20][C:21]([OH:23])=[O:22])[C:3]([CH3:31])=[CH:2][N:7]=1)[CH:16]([CH3:17])[CH3:18]

Participants

3

Reactant 1

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

Product 1

HCID 699643852-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

The title compound was prepared by a similar method to preparation 44 from benzyl 2-[3-chloro-5-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate [see preparation 61] and palladium hydroxide, to afford the product as a oil. LRMS: 323 (MH+)

Sources & evidence

ORD record
ord-706f702e133e4e888290c0c1d739c601
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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