Sodium hydride → N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2-(2-oxo-3-(3,3,3-trifluoropropyl) pyrrolidin-1-yl)acetamide

HRID 929311Notes

Reaction equation

HRID 929311 reaction equation
[F:1][C:2]([F:12])([F:11])[CH2:3][CH2:4][CH:5]1[CH2:9][CH2:8][NH:7][C:6]1=[O:10].[H-].[Na+].Cl[CH2:16][C:17]([N:19]([C:22]1[C:23]([Cl:33])=[N:24][N:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:26]=1)[CH2:20][CH3:21])=[O:18]>>[Cl:33][C:23]1[C:22]([N:19]([CH2:20][CH3:21])[C:17](=[O:18])[CH2:16][N:7]2[CH2:8][CH2:9][CH:5]([CH2:4][CH2:3][C:2]([F:1])([F:11])[F:12])[C:6]2=[O:10])=[CH:26][N:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[N:24]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 721939832-chloro-N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethylacetamideHCID 1046794123-(3,3,3-Trifluoropropyl)pyrrolidin-2-one

Product 1

HCID 118023540N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2-(2-oxo-3-(3,3,3-trifluoropropyl) pyrrolidin-1-yl)acetamide

Procedure

To 3-(3,3,3-trifluoropropyl)pyrrolidin-2-one in an appropriate reaction vessel may be added NaH (from about 1.0 eq to about 2.0 equivalent) in a solvent, such as THF (at a concentration between about 0.01 M to about 1 M) followed by 2-chloro-N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethylacetamide (from about 0.5 eq to about 1.5 eq). The reaction may be stirred at a temperature from about 0° C. to about 25° C. until determined to be complete. After completion of the reaction, the product may be obtained using standard organic chemistry techniques for workup and purification.

Workup

  1. concentrationsuch as THF (at a concentration between about 0.01 M to about 1 M)
  2. customThe reaction
  3. customAfter completion of the reaction
  4. customthe product may be obtained
  5. customfor workup and purification

Sources & evidence

ORD record
ord-3848f6599b694a1bb6fe02aae2b81860
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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