Triethylamine → (RS) Methyl 3-{6-[2-(3-acetoxy-4-nitrophenyl)-acetylamino]-pyridin-3-yl}-butanoate

HRID 49712Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH3:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C:15]([O:18][C:19]1[CH:20]=[C:21]([CH2:28][C:29](Cl)=[O:30])[CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26])(=[O:17])[CH3:16].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl.CCCCC>[C:15]([O:18][C:19]1[CH:20]=[C:21]([CH2:28][C:29]([NH:1][C:2]2[N:7]=[CH:6][C:5]([CH:8]([CH3:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=2)=[O:30])[CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26])(=[O:17])[CH3:16]

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of (RS) methyl 3-(6-amino-pyrid-3-yl)-butanoate (3.26 g, Reference Example 19) in dichloromethane (20 mL) at 10° C. was treated dropwise with a solution of (3-acetoxy-4-nitrophenyl)-acetyl chloride (4.32 g, Reference Example 17) in dichloromethane (30 mL) over 5 minutes. The mixture was stirred at 10° C. for a further 5 minutes then treated dropwise with triethylamine (2.47 mL) over 5 minutes. The resulting dark solution was stirred at room temperature for 1 hour, then left to stand overnight, then subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (3:2, v/v) to give the title compound (5.9 g) as a viscous gum.

Workup

stirringThe resulting dark solution was stirred at room temperature for 1 hour
waitleft
waitto stand overnight

Sources & evidence

ORD record: ord-aa480cc7b430496daf87d4c94538f9c9
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706738B2

Reaction notes

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