Acetic Acid → HCID 69003844, compound

HRID 225511Notes

Reaction equation

HRID 225511 reaction equation
CO[CH2:3][CH2:4][O:5][CH3:6].[C:7](/[C:9](/[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[CH:10]\[N:11]([CH2:19][C:20]([O:22][CH3:23])=[O:21])CCC(OCC)=O)#[N:8].[CH2:30]1[CH2:40]CN2C(=NCCC2)CC1.C(O)(=[O:43])C>>[NH2:8][C:7]1[C:9]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[C:10]([CH2:40][CH2:30][C:6]([O:5][CH2:4][CH3:3])=[O:43])[NH:11][C:19]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 80711,2-DimethoxyethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23122145HCID 23122145, compound

Product 1

HCID 69003844HCID 69003844, compoundYield 70%

Conditions

Temperature
60 °C

Procedure

To an ethylene glycol dimethyl ether (50 mL) solution of ethyl 3-{((1Z)-2-cyano-2-(3-pyridyl)vinyl)[(methoxycarbonyl)methyl]amino}propanate (6.236 g) was added 1,8-diazabicyclo[5,4,0]-7-undecene (3.590 g), and the mixture was stirred at 60° C. overnight. The reaction solution was cooled to room temperature and neutralized with acetic acid, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/5), to obtain the title compound (4.380 g, yield 70%). The NMR data and ESI/MS data of the compound are given below.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/5)

Sources & evidence

ORD record
ord-41352add16f3403abe5a7a49ecec2673
Source dataset
uspto-grants-2009_07
Patent number
US07557113B2

Reaction notes

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