Ethyl Acrylate → HCID 136507784, compound

HRID 530025Notes

Reaction equation

HRID 530025 reaction equation
[C:1]([O:5]CC)(=O)[CH:2]=[CH2:3].[CH3:8][C:9]1[C:10]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:11][NH:12][C:13]=1[NH2:14]>N1C=CC=CC=1.O>[CH3:8][C:9]1[C:10]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:11][N:12]2[CH2:3][CH2:2][C:1](=[O:5])[NH:14][C:13]=12

Participants

5

Reactant 2

HCID 8821Ethyl AcrylateHCID 178422057HCID 178422057, compound

Product 1

HCID 136507784HCID 136507784, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Ethyl acrylate (0.5 mL) was added to a solution of 4-methyl-3-(pyridin-3-yl)-1H-pyrazol-5-amine (300 mg, 1.72 mmol) in pyridine (4 mL) and water (1 mL) and the resulting mixture heated to reflux overnight. After cooling to rt, the solvent was removed in vacuo and the residue re-crystallized from MeOH to give the desired product: MS (m/z): 229.1 [M+H]+, 1HNMR (400 MHz, CD3OD) δ 8.80 (d, 1 H, J=1.2 Hz), 8.53 (dd, 1 H, J=1.2 Hz, J=4.8 Hz), 8.07-8.09 (m, 1 H), 7.52 (dd, 1 H, J=4.8 Hz, J=8.0 Hz), 4.36 (t, 2 H, J=7.2 Hz), 2.94 (t, 2 H, J=7.2 Hz), 2.13 (s, 3 H).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureto reflux overnight
  3. customthe solvent was removed in vacuo
  4. customthe residue re-crystallized from MeOH

Sources & evidence

ORD record
ord-cd2a5378c42e485d98d85c1dce90b51c
Source dataset
uspto-grants-2016_05
Patent number
US09351973B2

Reaction notes

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