Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate → Benzyl 2-[3-[(1S)-1-benzyl-2-(dimethylamino)ethyl]amino-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate

HRID 567811Notes

Reaction equation

HRID 567811 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][N:4]([CH3:6])[CH3:5].[Cl:14][C:15]1[N:20]=[C:19](Cl)[C:18](=[O:22])[N:17]([CH2:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[C:16]=1[CH3:34]>>[CH2:7]([C@H:2]([NH:1][C:19]1[C:18](=[O:22])[N:17]([CH2:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[C:16]([CH3:34])=[C:15]([Cl:14])[N:20]=1)[CH2:3][N:4]([CH3:6])[CH3:5])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 11251722(1S)-1-Benzyl-2-(dimethylamino) Ethylamine

Product 1

HCID 59900581Benzyl 2-[3-[(1S)-1-benzyl-2-(dimethylamino)ethyl]amino-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetateYield 51.8%

Procedure

The title compound was prepared by a similar method to preparation 18 from N-[(2S)-2-amino-3-phenylpropyl]-N,N-dimethylamine (190 mg, 1.07 mmol; prepared as described in Chem. Pharm. Bull. 1970, 18,1731-1736) and benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preparation 17) (361 mg, 1.10 mmol). The crude product was purified by chromatography (SiO2; gradient elution 100% hexane; 80:20 hexane:ethyl acetate; 60:40 hexane:ethyl acetate; 40:60 hexane:ethyl acetate; 20:80 hexane:ethyl acetate) to give the desired product (yellow solid, 260 mg, 50%). 1H NMR (CDCl3) δ 2.20 (m, 9H), 2.30 (m, 1H), 2.20 (m, 1H), 2.85 (m, 1H), 3.10 (m, 1H), 4.25 (m, 1H), 4.80 (s, 2H), 5.20 (s, 2H), 6.20 (m, 1H), 7.20 (m, 5H), 7.35 (m, 5H). LRMS m/z=469.2, 471.3 (M+1)+.

Workup

  1. customThe crude product was purified by chromatography (SiO2; gradient elution 100% hexane; 80:20 hexane:ethyl acetate; 60:40 hexane:ethyl acetate; 40:60 hexane:ethyl acetate; 20:80 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-558385190b684af884034db478607b32
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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