Dimethylformamide diethylacetal → 3-(Dimethylamino)-2-(2-methylpyridin-3-yl)-acrylic acid ethyl ester

HRID 889301Notes

Reaction equation

HRID 889301 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:7]([CH3:12])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].C(O[CH:17](OCC)[N:18]([CH3:20])[CH3:19])C>>[CH2:1]([O:3][C:4](=[O:13])[C:5]([C:6]1[C:7]([CH3:12])=[N:8][CH:9]=[CH:10][CH:11]=1)=[CH:17][N:18]([CH3:20])[CH3:19])[CH3:2]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 15169545Ethyl 2-(2-methylpyridin-3-yl)acetate

Product 1

HCID 687047223-(Dimethylamino)-2-(2-methylpyridin-3-yl)-acrylic acid ethyl ester

Procedure

600 mg (3.35 mmol) of the compound from Example 39A are heated in 1.7 ml (10.0 mmol) dimethylformamide diethyl acetal overnight at 100° C. After cooling, the mixture is concentrated and the residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. customthe residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-c7874aaac0c1419e922b6b0c11a6cdf2
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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