Dimethylformamide diethylacetal → ethyl 2-(4-cyano-1H-pyrazol-1-yl)-3-(dimethylamino)acrylate

HRID 526402Notes

Reaction equation

HRID 526402 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=1)#[N:2].C(O[CH:17](OCC)[N:18]([CH3:20])[CH3:19])C>>[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:8](=[CH:17][N:18]([CH3:20])[CH3:19])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=1)#[N:2]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 117600226ethyl 2-(4-cyano-1H-pyrazol-1-yl)acetate

Product 1

HCID 117601152ethyl 2-(4-cyano-1H-pyrazol-1-yl)-3-(dimethylamino)acrylateYield 89%

Procedure

Combined ethyl 2-(4-cyano-1H-pyrazol-1-yl)acetate (0.427 g, 2.383 mmol) with 1,1-diethoxy-N,N-dimethylmethanamine (1.403 g, 9.53 mmol) and heated in a closed vial at 100° C. for 2.5 h. The mixture was concentrated in vacuo and purified using flash column chromatography on NH silica gel (30 g SiO2, EtOAc in heptane, 10-50% gradient) to give the title compound (0.4942 g, 89% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12 (t, 3H) 1.91-2.43 (m, 3H) 2.70-3.29 (m, 3H) 4.03 (q, J=7.07 Hz, 2H) 7.59 (s, 1H) 8.14 (s, 1H) 8.56 (s, 1H). MS m/z [M+H]+ 235

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified

Sources & evidence

ORD record
ord-b9ca4f13d3a14aa688bdcc12cb00c9bf
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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