Pyridine → HCID 118023006, compound

HRID 929294Notes

Reaction equation

HRID 929294 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:14][CH3:15])[C:8](=[O:13])[CH2:9][CH2:10][NH:11][CH3:12])=[CH:5][N:4]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1.N1C=CC=CC=1.[F:28][C:29]([F:35])([F:34])[CH2:30][C:31](Cl)=[O:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[Cl:1][C:2]1[C:6]([N:7]([CH2:14][CH3:15])[C:8](=[O:13])[CH2:9][CH2:10][N:11]([CH3:12])[C:31](=[O:32])[CH2:30][C:29]([F:35])([F:34])[F:28])=[CH:5][N:4]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 27833433,3,3-Trifluoropropionyl chlorideHCID 86700623HCID 86700623, compound

Product 1

HCID 118023006HCID 118023006, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-(methyl amino)propanamide (0.070 g, 0.23 mmol) in dry CH2Cl2 (0.76 mL) was cooled to a temperature of about 0° C. under N2. To the solution, DMAP (0.014 g, 0.11 mmol), pyridine (0.028 mL, 0.34 mmol), and 3,3,3-trifluoropropanoyl chloride (0.026 mL, 0.25 mmol) were added sequentially. The reaction was slowly warmed up to room temperature under N2, then stirred at room temperature overnight. The reaction was diluted with water (2 mL) and stirred for five minutes. Layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×2 mL). The combined organic extracts were dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0%-5% MeOH/CH2Cl2 to afford the title compound F102 as a white semi-solid (0.062 g, 63%).

Workup

  1. stirringstirred for five minutes
  2. customLayers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×2 mL)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 0%-5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-daf433ebf04b4d089cc27ad89fa12c67
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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