Ammonia → (2S)-3-[4-(3-amino-5-methylphenyl)-1H-pyrazol-1-yl]-2-hydroxypropanamide

HRID 595293Notes

Reaction equation

HRID 595293 reaction equation
[NH3:1].FC(F)C1C=CN=C([NH:10][C:11]2[CH:12]=[C:13]([C:18]3[CH:19]=[N:20][N:21]([CH2:23][C@H:24]([OH:29])[C:25](OC)=[O:26])[CH:22]=3)[CH:14]=[C:15]([CH3:17])[CH:16]=2)N=1>>[NH2:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:19]=[N:20][N:21]([CH2:23][C@H:24]([OH:29])[C:25]([NH2:1])=[O:26])[CH:22]=2)[CH:14]=[C:15]([CH3:17])[CH:16]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 131734585methyl (2S)-3-[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]-2-hydroxypropanoate

Product 1

HCID 118208773(2S)-3-[4-(3-amino-5-methylphenyl)-1H-pyrazol-1-yl]-2-hydroxypropanamide

Conditions

Temperature
60 °C

Procedure

Ammonia (7.0 M in methanol, 1.5 mL, 10.5 mmol) was added to a flask containing methyl (2S)-3-[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]-2-hydroxypropanoate (57.2 mg, 0.14 mmol) and the mixture was stirred overnight at 60° C. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (0 to 95% ACN/water with 0.1% TFA modifier) to afford (2S)-3-[4-(3-amino-5-methylphenyl)-1H-pyrazol-1-yl]-2-hydroxypropanamide. MS ESI calcd. for C13H17N4O2 [M+H]+ 261. found 261.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by reverse phase HPLC (0 to 95% ACN/water with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-b65979517e234067bd5a1d1aec34add2
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

Loading…