Hydrochloric Acid → N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2-hydroxypropanamide

HRID 929305Notes

Reaction equation

HRID 929305 reaction equation
C([O:4][CH:5]([CH3:23])[C:6]([N:8]([C:11]1[C:12]([Cl:22])=[N:13][N:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:15]=1)[CH2:9][CH3:10])=[O:7])(=O)C.[OH-].[Li+].Cl>CO.C1COCC1>[Cl:22][C:12]1[C:11]([N:8]([CH2:9][CH3:10])[C:6](=[O:7])[CH:5]([OH:4])[CH3:23])=[CH:15][N:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 867005991-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)amino)-1-oxopropan-2-yl acetate

Product 1

HCID 86700598N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2-hydroxypropanamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)amino)-1-oxopropan-2-yl acetate (2.4 g, 7.1 mmol) in MeOH (9 mL) and THF (9 mL) was added lithium hydroxide (LiOH, 2 M, 7.0 mL, 14 mmol). The reaction mixture was stirred for two hours at room temperature, and then the reaction mixture pH was made neutral by the addition of aq. 2M HCl. After the mixture was then extracted with EtOAc, the organics phases were combined, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound C13 as a white solid (1.9 g, 88%): mp 137-138° C.; 1H NMR (400 MHz, DMSO) δ 9.08 (d, J=2.5 Hz, 1H), 8.98 (s, 1H), 8.58 (dd, J=4.7, 1.1 Hz, 1H), 8.23 (ddd, J=8.4, 2.6, 1.3 Hz, 1H), 7.59 (dd, J=8.3, 4.7 Hz, 1H), 4.97 (d, J=7.6 Hz, 1H), 4.08 (m, 1H), 3.57 (d, J=50.6 Hz, 2H), 1.10 (d, J=6.5 Hz, 3H), 1.07 (t, J=7.1 Hz, 3H); ESIMS m/z 295.6 ([M+H]+).

Workup

  1. extractionAfter the mixture was then extracted with EtOAc
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4120710fcb60476e9bae928740b96be3
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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