Water → HCID 21934522, compound

HRID 1241444Notes

Reaction equation

HRID 1241444 reaction equation
[C:1]([CH:3](C(OCC)=O)[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:14]([CH3:15])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[C:10]=2[N:23]=1)#[N:2].[OH-].[K+].O.CCOC(C)=O>C(O)CO>[CH3:15][N:14]1[CH2:13][CH2:12][NH:11][C:10]2[N:23]=[C:6]([CH2:5][CH2:4][CH2:3][C:1]#[N:2])[CH:7]=[CH:8][C:9]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 14797Potassium HydroxideHCID 21934570HCID 21934570, compound

Product 1

HCID 21934522HCID 21934522, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of tert-butyl 6-(3-cyano-4-ethoxy-4-oxobutyl)-1-methyl-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxylate (5.78 g, 14.88 mmol) and KOH (powder, 1.25 g, 22.32 mmol) in ethylene glycol (30 mL) under N2 was heated at 150° C. for 3 hours. The mixture was cooled to 0° C. and portioned between water and EtOAc. The organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. Flash chromatography (silica, 100% EtOAc) yielded a colorless oil (2.2 g, 66% yield). H NMR (CDCl3) δ 2.00 (t, 2H), 2.32 (t, 2H), 2.63 (t, 23H), 2.32 (s, 3H), 3.20 (t, 2H), 3.56 (t, 2H), 6.40 (d, 12H), 6.58(d, 1H), 4.20 (t, 2H), 6.41 (d, 1H), 6.89 (d, 1H).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f884dda5fed544c68af7dca7da794f05
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

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