Sodium Bicarbonate → HCID 118023154, compound

HRID 929295Notes

Reaction equation

HRID 929295 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:25][CH3:26])[C:8](=[O:24])[CH2:9][CH2:10][CH:11]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[C:12]2=[O:23])=[CH:5][N:4]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[N:3]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:6]([N:7]([CH2:25][CH3:26])[C:8](=[O:24])[CH2:9][CH2:10][CH:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:23])=[CH:5][N:4]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[N:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 118024035HCID 118024035, compound

Product 1

HCID 118023154HCID 118023154, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of tert-butyl 3-(3-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)amino)-3-oxopropyl)-2-oxopyrrolidine-1-carboxylate (0.076 g, 0.17 mmol) in dry CH2Cl2 (0.33 mL), TFA (0.33 mL) was added at room temperature under N2. The reaction was stirred at room temperature for about 90 minutes. Saturated aqueous NaHCO3 (about 10 mL) was carefully added until reaction mixture became basic. The product was extracted with CH2Cl2 (3×10 mL), dried and concentrated. The residue was purified by silica gel chromatography by eluting with 0%-15% MeOH/CH2Cl2 to afford the title compound F131 as a white foam (0.041 g, 66%).

Workup

  1. extractionThe product was extracted with CH2Cl2 (3×10 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washby eluting with 0%-15% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-8cc1c6989a944c348430a87b725a8721
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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