2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → HCID 13557967, compound

HRID 1914852Notes

Reaction equation

HRID 1914852 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:11]([C:13](=[CH:19]OCC)[C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]>C(O)(=O)C>[NH2:12][C:11]1[N:7]2[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=[C:8]2[N:10]=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 178441179HCID 178441179, compound

Product 1

HCID 13557967HCID 13557967, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-tert-butyl-1H-pyrazol-5-amine (484 mg, 3.48 mmol, 1 eq.) and ethyl 2-cyano-3-ethoxyacrylate (590 mg, 3.49 mmol, 1.00 eq.) in acetic acid (10 mL) was stirred for 16 h at 100° C. under nitrogen. After cooling, the resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to 8 with saturated aqueous NaHCO3 solution and extracted with ethyl acetate (100 mL×3). The organic layers were combined, dried and concentrated under reduced pressure. The residue was applied onto a silica gel column with CH2Cl2/MeOH (30:1) as an eluent to obtain the corresponding product as a white solid: LCMS (m/e) 263 (M+H); 1H NMR (300 MHz, DMSO-d6) δ ppm 8.56 (s, 1H), 8.40-8.38 (broad, d, J=6.0 Hz, 2H), 6.48 (s, 1H), 4.33 (q, J=7.2 Hz, 2H), 1.37-1.31 (m, 12H).

Workup

  1. temperatureAfter cooling
  2. concentrationthe resulting mixture was concentrated under vacuum
  3. extractionextracted with ethyl acetate (100 mL×3)
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-748ec595af5543afa7e0d7a6e9614492
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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