Sodium hydride → HCID 118023952, compound

HRID 929313Notes

Reaction equation

HRID 929313 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:18][CH3:19])[C:8](=[O:17])[CH2:9][CH2:10][CH:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])=[CH:5][N:4]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:3]=1.[H-].[Na+].FC(F)(F)S(O[CH2:34][C:35]([F:38])([F:37])[F:36])(=O)=O>C1COCC1>[Cl:1][C:2]1[C:6]([N:7]([CH2:18][CH3:19])[C:8](=[O:17])[CH2:9][CH2:10][CH:11]2[CH2:15][CH2:14][N:13]([CH2:34][C:35]([F:38])([F:37])[F:36])[C:12]2=[O:16])=[CH:5][N:4]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 118023154HCID 118023154, compound

Product 1

HCID 118023952HCID 118023952, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-(3-Chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-(2-oxopyrrolidin-3-yl)propanamide (0.037 g, 0.10 mmol) was added to a vial with stir bar, followed sodium hydride (60% in mineral oil, 0.010 g, 0.26 mmol). The vial was placed under N2 and chilled to 0° C. THF (1 mL) was then added and the reaction was allowed to stir for 30 minutes 2,2,2-Trifluoroethyl trifluoromethanesulfonate (0.037 mL, 0.26 mmol) was added neat, dropwise. The reaction stirred overnight. The reaction was adsorbed onto CELITE®. Purification by flash column chromatography using MeOH/CH2Cl2 as eluent provided the title compound as a colorless oil (0.011 g, 24%).

Workup

  1. additionwas added neat
  2. stirringThe reaction stirred overnight
  3. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-1170ab78f8914c0eb66faef8e1f9eeea
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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